Renting properties for STR does not come with the upsides of tax savings, appreciation, equity build up, etc.I agree with the sentiment expressed by others that diving straight into STR, especially with a property that is cashflow negative as a long-term rental (LTR) or through arbitrage, can pose risks.

I have a mailing list of over 3000 recipients and are aiming for a personal touch with letters that appear handwritten and are signed in ink.

But at times can be a good place to start to build up a portfolio and future cash for investment instead of waiting for your equity or the world to decide we can have low interest rates… which sounds like that’s what you are suggesting for me to do.

South facing houses/streets (like on the side of a hill facing south) get less ice build up. 

@Jim Pellerin talked about how you can use SFH flips to build up funds to get into multifamily. 

But if you're living at home then it may be fine to build up the equity.

I also had reason to believe I could hit $7500 or $8000 on this property (not 100% that I could, but a buddy was doing similar numbers in a similar property but also being less discerning with guest screening and had a longer run time to build up reviews).If my end profit was $5000+ a month, the headache seems more palatable.But, when Airbnb decided to give a no questions asked refund on $20,000 on confirmed “strict” bookings, and the str market tanked, I switched over to LTR and haven’t looked back.

That said, we don't need to be next to family but being somewhat close by has advantages so those places are favored somewhat.The strategy is to buy, househack a value-add multifamily for 2 years then rinse and repeat until we can build up enough capital to either start developing, move to larger multifamily or the wife wants to start a senior care facility. 

Watch out for build-up of humidity.

@Barb Knowles If you're just starting out, you may want to build up more cash before you start buying and holding if funds are low.