Self managed HOAs are usually undercapitalized so you want to take a thorough review of the condition of the community to make sure there isn’t deferred maintenance because you might get hit with a special assessment if the board isn’t setting aside cash for those capital improvements.At face value, taking into consideration my typical financial objectives, I wouldn’t do this deal unless it was a much lower price.

We're looking to gather info about likely cost, pitfalls, time required, considerations when obtaining financing, etc. 

If your new LLC is a disregarded entity (single-member or owned solely by you and your spouse in a community property state), it won’t trigger a taxable event, and you’ll continue reporting income on your personal return.

I’m giving serious consideration to converting into a PadSplit.However, I have heard that Fort Worth (the city, Tarrant County, the faceless boogey man…) has issues with PadSplit whereas Dallas County is supportive.I would love to hear about your experiences between the two markets and if Fort Worth can be viable for PadSplit and anything I should be mindful of?

If I had an answer to my money issue then I would quickly pull the trigger on a good deal. 

.- Does anyone see any flaws or can offer some improvements/considerations to the financing strategy of this plan? 

We are going to give it a try, but if we choose to either STR the property a bit with some personal use OR live in the property either some STR in 2025, does that trigger recapture or is it only on sale?

My Wife and I are going to pull the trigger in 2025 and are looking in the Central PA area to buy our first STR.

Is this something I should take in consideration? 

Adding the ex to the title could trigger gift tax implications, so keeping it simple is best.