Hello, I am new to real estate investing and I have a tentative verbal deal on a pre-market lake property that I would eventually like to make my retirement home (10 years or so).

I previously relied on 3rd party GC's building quite a few single family to 4 unit buildings throughout Philadelphia and eventually transitioned to self performing.

If you continue keeping it cash flow will improve and eventually there will be good cash flow.  

The banks and gov't and businesses will eventually lend and create the next bubble. 

Im interested in wholesaling so that I can use that income to invest back into real estate and eventually become an investor and full time entrepreneur.

That strategy lets you make chunks of cash on each flip, which also gives you cash to buy your next flip, and then eventually you have enough money to buy a long term hold you can rent out for more passive income than flips.  

So buying a 450k home in Pittsburgh means that eventually the property will be taxed at an assessment value of 240k, which is close at 5k.

I want to be able to eventually invest in real estate and become financially independent.

But between you paying down your mortgage, plus the tax write offs, plus market appreciation it sets you up for having tens of thousands of dollars in tax free gains when you eventually sell it.  

Eventually your annuity/stock is AT LEAST $3m basis (from the refinances and the sales) not to mention growth and reinvestment.