I know all this deferred tax must be repaid if I were to sell without a 1031, so that tips the scales in favor of the DST option. 

Hi BP, I've been trying to research a straight answer on this but can't seem to find a direct one.

Anyone tried this?

Our HOA by laws state that I cannot rent my primary residence, I must sell it in our community.

My realtor who is also the selling agent, said she tried getting info form the lawyers and the Hoa. but no one is giving her a straight answer.

That's the approach a successful DIY landlord must incorporate.

You can try PenFed -- they had halted lending on investments until 2024 so they may be lending on investments now. https://www.penfed.org/You can also do a cash out refinance.

Each deal you make should always be self sustaining, that means if you only owned one of these properties, and it doesn't matter which one, it must support itself.Negative CF means you have "other" properties supporting a property, or worse, you have your own cash supporting a property you own. 

My question is, is it worth trying to rent the house out or should I sell and try to get into a fixer upper in town where there’s more to do?  

Before joining, I spent about 18 months listening to podcasts, reading posts and books, etc. trying to teach myself.