@Mike Miller Are you planning to purchase properties in the bay area?

Like Mike Tyson said "everyone has got a plan until they get punched in the face."

But it’s awesome that you’ve got a plan and are ready to make it happen!

Where I am looking for guidance is we plan on using a larger down payment of at least 50% to be on the conservative side of leverage.

However, for a primary, especially if you plan to be there a while then it may be worth the hassle.

What I'm most concerned about is the Project 2025 plan to gut HUD and most social services.

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.  

I plan for a time when they can be there and check in and make sure there aren't any maintenance items they haven't told me about.

If you plan to do the work yourself, then that is where is becomes less clear especially if a buyer feels you did a less than 100% professional job.

However it is important to remember to make sure you have a plan to pay that loan down and not allow that credit card debt to climb back up.