If you advanced to D.III, your financial situation would improve to the appropriate level for that division.
You most likely wouldn't be winning the title that 1st season, but you wouldn't be a minnow either.
Glancing at your roster (without seeing any stats, obviously), there are plenty of players on the market that could improve your roster without breaking the bank.
NO ONE at this table ordered a rum & Coke
Charles: Penn has some good people
A CT? Really?
Any two will do
Any three for me
Any four will score
Any five are live