We've been car-free for many years and want to avoid owning a car as long as possible!

Will,That's a question that involves a lot of detail and conversation to map out the LLC, Financing, Grants, and percentage of partnership should you decide to acquire more than 5-10 properties.Feel free to reach out if you want to discuss the scenario and I can try and detail some tips from my experience. 

If you purchased from the party who purchased at the tax sale you probably would have received a SWD because the Grantor would not have wanted to warrant anything other than the Grantor's actions.While I'd be surprised if a county employee opined on the status of your title, there may be a difference between having a clear title (one without a current challenge) and insurable title (one free of significant possible risk of being challenge in the future). 

Like you mentioned, be aware of the short-term rental regulations through the city but also pay close attention if there is an HOA.

. - probably about one third of DSCR lenders are STR friendly at this point (most will not do STR or have very conservative UW)Short-Term Rental Loans: What Are the Options and How Do DSCR Loans Stack Up?

So you get 57% of $400k tax free and pay tax on $172k. 

If you are need of a good reliable contractor please feel free to reach out to me.

If you have any questions feel free to send me a DM. 

Please feel free to use code VENI324 when upgrading to get your investing career going!

So in the short term, my objective is to end up with a cash flowing property.