The rental had ratty furniture, a record player prominently featured in the marketing but it had no speakers, missing basics items in the kitchen, lots of drunks in the concrete hallways that reverberated right into the bedroom at 2am, a strong odor of urine outside, and more.We have super hosts in this forum that have hundreds of 5-star reviews and are masters of the craft, but I look at their rentals and see they don't have any artwork on the walls, decor is basic, they do nothing to make the guest feel welcome, etc. 

@Na Connolly, talk to an eldercare lawyer there are likely multiple issues to consider here.

I could feasibly pursue multiple deals and if I find one in an area I’d like to live once I move back to the US, I would like the option of renting it out while still living abroad but being able to move in and refi to a better deal with an owner-occupier loan.   

For example, if you're planning a kitchen remodel, get multiple quotes to ensure you have a solid grasp of what it will actually cost.3.

Comparing workload, a multi-unit property will still require showings, maintenance etc for multiple units.

Despenas LLC aka SDIRA Wealth aka Modern Day Living Real Estate LLC are all scam companies that inflate housing prices in the neighborhood only to sell eviction-prone extremely damaged homes with no intent to perform the agreed-upon inspection repairs and send you through multiple corporate hoops after purchase only to completely ignore you immediately after the sale.

House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

Quote from @Chris Seveney: @Charlene Kingsnorth have you had an sec attorney also review what you are doing as if you're are having multiple people as part of a loan participating in it depending on the state this could get you in hot water - so be careful  good point Chris some state allow fractionalized deed of Trust mortgages other do not or require PPM like documents prior to offering them..

Taylor sent multiple email inquiries to our insurance provider asking what risks their policy covered.

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?