We originate loans with 100+ lenders and will tell you that you cannot have All of the above :) Just set top 2-3 points of what matters to you most and that can help you in selecting which broker/lender to go with.

In an effort to bring ANY $ in to help cover the mortgage ($4600 including taxes and insurance), I put together an AirBnB site for the property and set it live, with zero expectation.

I also value the planning element, especially if I’ll be setting up a trust, so now I feel torn about which option is best.EAs aren't going to focus on auditing and planning.

Depending on the built in gain and how long you've lived there, you should be able to sell your current primary tax-free and roll any gains from that into your new primary residence, that is IRC section 121.Is there a set amount of time before you can move into the rental as your primary?

I got a doctor who was all set up long term lease NNN personal guarantee of someone with wherewithal. 

Total rent between the three is $3200/month.I have an adjustable 20 year mortgage with a balance of $100,000~ at 4.95% that is set to adjust in 2026.I also have a HELOC on that property at $180K~ with a 9.75% rate. 

For my rental in New Jersey, I have set a deductible of $60 whenever I make a visit to do any kind of repairs for the tenant.

It sounds like they have money, and it sounds like in exchange for that money you're setting them up with an income stream.

I recommend you set up your BP alerts so anything Chicago will show up on your feed. 

I know as the Lender, I always have the option to modify things but the NoD helps set the stage if the borrower doesn't act or respond in a way I feel is beneficial to getting the project across the finish line and me my capital back.