Yeah when I was considering my own backyard, I was trying to avoid cities that required relocation assistance, and other weird laws.

For example, places like Illinois and Oklahoma have specific rules requiring a real estate license for certain types of marketing.This specifically for flipping land using Transactional Funding.If you’ve done this before, what states have you found to be friendly toward this approach?

The only item I would suggest is double check the payment terms of the your HELOC... in particular, can you pay interest only or are you required to pay a portion of principle each month on the amount utilized.

Success in real estate requires courage, perseverance, and the willingness to take calculated risks.Internalize these principles and apply them in your real estate endeavors, and you will be on your path to success.

The Sonyma FHA loan, if you refi the loan, move from before the 10 year requirement, etc.

While a more robust conversation around your entire financial picture would be required, here are a few questions that I'd want to double click on first:Where is Your War Chest?

Flat out, I realize we're friends/family, but I need this lease in place to comply with laws that require things in writing and for my protection should there ever be issues.

The key to this is finding a HML that doesn't require access to the property for an appraisal.

Banks so far have required me to come in person to open account. 

If cash flow is your priority, out-of-state investing in more affordable markets like the Midwest or Southeast might make sense, though managing from a distance requires a solid local team.If you stay local, networking will be key since the best deals in expensive markets rarely come from the MLS.