But how good has the Blues’ business to date been, what’s still to come and how worrying is the spending power of some of Pompey’s key arrivals?
They’re some of the key questions that need answers – so thankfully Jordan Cross stepped up to provide his thoughts on these important issues.
Here’s what he had to say...
Q There's less than two weeks to go until the start of the season. How would you rate Danny Cowley s transfer window to date?
I'm going to start on a positive note because I must admit there's a fair few negatives creeping in with 10 days to go.
If you look at Danny’s business to date, I think it’s good business, I like what he's done so far.
Clark Robertson - I've been impressed with what I've seen from him so far.
He was excellent against Luton on Saturday, very progressive in his passing, aggressive in his defending, calm on the ball, very composed, and he's done everything he’s needed to do so far in terms of the question marks over his injuries and rehabbing properly to ensure he doesn’t go down that road again.
Ryan Tunnicliffe looks very dynamic, has Championship experience, with Shaun Williams looking composed on the ball, Freeman, too - they all look very good signings with Championship experience.
The punts have come in perhaps Liam Vincent and Jayden Reid, who picked up a cruciate injury on Saturday.
Gassan Ahadme, of course, is the one who everyone is talking about with eight goals so far this pre-season.
We don't want to put too much pressure on his shoulders, but he looks like a promising figure.
Meanwhile, Gavin Bazunu was probably Pompey's best player (against Chelsea under-23s) and the best player involved - very composed with his feet, very quick and agile around the box, sharp coming out and you could hear him talking the whole way through the game.
So some real positive work done so far, but I have to caveat that severely with the massive amount of work still to do.
There’s huge holes in Danny Cowley’s squad still.
Q As you said, there's gaps still to be filled - but will Cowley stick to his principles and wait to bring in the quality he craves or will he have to compromise on that front?
He's very emphatic about this, Danny Cowley - he's absolutely not willing to compromise.
He's very emphatic he can get players in and I'm hearing names of players being offered to Pompey - one or two who would be excitable to supporters - but Danny Cowley is not interested in these players.
He wants players he feels will fit the bill for Pompey and the way he wants to play – and he's being uncompromising on it.
With that in mind, Danny has missed out on targets, missing out on a number of big names.
But he does his due diligence and that's why he spends so much time in the data room trying to build this list of players.
So they haven't compromised yet because if they miss out on target A, B or C, they've got D and E.
Danny says he has a list of five names and when that list goes they move on to another five.
In that respect, he's missing out on players and has been 'blown out of the water' so they have to move down the list.
But he's not going to drop down and then just get bodies in - and there's a lot of strong talk from Danny on that note.
I think he would rather go without than have players he feels are not up to the requite standard.
Q Is Danny Cowley surprised at the difficulty of the task he's undertaken and how much of a worry is the business that Ipswich, Wigan etc are able to do this summer?
This is not a criticism, but I think Pompey have been caught out slightly by the nature of the business in League One.
I don't think anyone saw the extent at which Ipswich, Wigan and to a lesser extent Sunderland (have been operating).
I'm hearing Sunderland bid £1.3m for a player at the weekend; Charlie Wyke has gone to Wigan with a huge signing-on fee; Ipswich produced a big signing-on fee for Joe Pigott - a player Pompey were interested in.
I think Pompey knew it was going to be competitive with those takeovers but I don’t think they saw it happening to the extent that it has.
That's been a frustration because I know Pompey are sticking rigidly to their budget, they're not going to go with these clubs with their takeovers and are being bankrolled.
Pompey are being run on a sustainable basis, so it's an understandable frustration among supporters when they see clubs that they should be punching their weight with going out and bringing in players at Pompey's expense.
There is a degree of frustration from Danny, I feel. But he's more of a solutions man.
He's not one to moan about it too much, he just wants to find a way and be as competitive as he possibly can.
He's looking around it and he has been keen to point out that, with his previous successes in football, it's not been done on the biggest of budgets.
He's found a way to do it, he's found a way to be competitive and that's the challenge for Danny.
When you hear over the past couple of days that Danny has missed out on a significant loan addition because he was 'blown out of the water' by a rival, everything points to that rival being Ipswich Town following their acquisitions of George Edmundson and Conor Chaplin.
The player being mentioned was offered double in terms of wages to what Pompey could offer, and it was a permanent move. Pompey can't compete with that.
So when you're getting close to players then that's going to agonise supporters, let alone the manager.
But Danny's got to park that and push on - and I think that's where his mind set is at at the moment in terms of finding solutions.
Q Undoubtedly some departures would help - is there any further development on that front?
The phrase I've been using with our media colleagues is it's a 'moveable feast'. There's definitely things in the pipeline.
You can see Ellis Harrison becoming a live one again.
We know Ipswich are still coming on strong for Michael Jacobs. He did speak at the weekend about focusing and settling down at Portsmouth and it had gone quiet, but my understanding is Ipswich are still keen on Michael Jacobs.
Meanwhile, with Ronan Curtis, I felt it was always going to run late into the window.
It's also worth noting, with a tight budget, Danny Cowley might still be forced to push one or two out on loan, which he wouldn't otherwise have done, just to free up a little bit more money to get the players in the key areas he needs.
Q You mentioned the positive signings already made this summer by Pompey - but are they the best signings Pompey fans can expect or is there other notable arrivals still to come?
I think Danny is still after players with Championship nous and they can pay wages of £5,000 - £5,500 per week and you can get decent players on that amount.
I think there's time still. I think they're going to move into the loan market, which will be a key market for Portsmouth.
But they've got to be competitive. We've got 10 days until the season starts, we had a team full of triallists play on Tuesday night and we shouldn't be in a situation where triallists, who in my mind won't be here next season, are being played.
But they need those players and those bodies at the moment.
It is a concern to have that amount of triallists around when we should be settling the team - so a massive amount of work still needs to be done and I need to sound that warning.
There's so much work still to do and maybe we'll see Pompey finding it hard to hit the ground running as a result, which is a major concern for me.
So as much as I'm optimistic about the signings that have already been done, I have to sound a note of caution where Pompey stand at the moment – the amount of work still to be done, the strength of their key rivals in probably the toughest division in a decade.