Either1) your startup takes off and you can distribute profit fast enough to pay off your debts, or2) you find another source of $100,000 a year (which barely even starts to pay down the $300k, but might provide a better chance for a better loan), or3) you BK and possibly lose the rental houses to creditors (hopefully not, but we don’t know how they are held), or 4) you sell the houses, take the tax hit, work with the IRS on a payment plan whose interest will be much lower than your CCs, and focus on the startup.  

While Redfin isn’t the most reliable source for estimating the values it indicates that I have about 400k in equity.

The main property will be my primary residence.My biggest question is, what kind of foundation would you use, (that is to code and will pass inspection/permits in Charlottesville) that is either relatively easy DIY or cheap to outsource.

Don’t discriminate on source of income.

How are your sourcing deals?

But you have to be very creative and understand that if you're seeing deals from industry professionals (rather than sourcing them yourself), there's probably not enough meat left on the bone for a good opportunity to create value.Good luck!

If you are borrowing for renovations, you will likely have a draw fee in the $100-300 range per draw.Selling costs: biggest one is commissions.  

Updating Failed/troubled projects stastistics with some more info from community and public sources:1.

What are the biggest pitfalls I should look out for? 

You can find sources that have contracts for any given state, but you want to also know they are well vetted and up to date with recent changes in laws.