Usually, these are tied to your paycheck too which makes the payback simple as long as you are working at that company during the entire payback period. 

This is really not a big deal at all and to be honest I wouldn't do any extra paperwork or anything.

HSA holders 55 and older can contribute an extra $1,000 to their HSAs.Also in 2024, the IRS increased the standard deduction by $1,500, to $29,200, for married couples filing jointly, plus $1,550 for each spouse 65 and older.

Covering Costs is also a plus as the rent from Airbnb can help pay your mortgage and even give you extra cash.

Not saying with the proper structuring it can't be done, but there are usually more effective ways.

The downs, usually are worst than the ups.

Your first response is to spend thousands extra in legal fees to get back to where you were before you asked for a discount on a properly priced property.  

I pay $4100/mo not including utilities. 1 year appreciation according to all 3 real estate websites zillow, redfin, and realtor.com, my house is worth about $645k.I've been house hacking by renting out my additional 2 bedrooms to mid term rentals (usually 6mo stays) and brought in about $9k for the first year.

If you know you want to get into STRs, find properties in your market or market of interest that are managed by Vacasa and Evolve that are underperforming and have guest feedback indicating the the customer service from the host was poor (as it usually is with the big national STR PMs), look up the owner's name on the county or city tax records, and cold call or text them.

I can help with cold calling.Cost per lead is usually going to be in the $20-$50 dollar range (assuming a VA cold caller with native English) and a cost of about $0.20 per record for them to call potential motivated sellers (high equity, certain age, etc).CAC is going to depend on your conversion skills, but within 3-6 months can be $1500 to $5K depending on how many leads it takes you to close them.