If someone originally loaned you $5K and then received $6K when you flipped the property, issuing a 1099 for $6K could cause them to pay taxes on the full amount, rather than just the $1K profit they earned.A cleaner way to structure this might be to have them buy into the partnership instead.

Build your STR core four (agent, cleaner/handyman, co‑host or PM, CPA who knows REP/STR rules), create a punch‑list template to stabilize this fourth unit fast, and commit to weekly pricing reviews and monthly P&L checks so you can rinse and repeat with confidence.

Also the amount of wood the first guy is allowing for.

Practical path: confirm rules with the custodian, price the deal with conservative leverage, get term sheets from lenders who specialize in nonrecourse to retirement accounts, and decide if lending your SD funds to an unrelated investor is cleaner for your first move.

It is a studio style tiny home on 5 acres, designed as a high-end couples retreat in the woods.

Prioritize value that boosts NOI and appraisal without heavy disruption: pave or gravel the drive for cleaner parking, replace unsafe stairs/decks or at least tighten, paint, and add railings, and give the exterior a quick win with lighting, mailbox numbers, and simple landscaping for curb appeal.

Hey everyone,I’ve been hosting in Denver for a while and currently have a 4.97 star average with Superhost status, and lately I’ve been curious about what other hosts find most challenging when managing short-term rentals.For me, it took some time to find the right team (cleaner + handyman).

For investors, this means:You don’t have to waive contingencies.You can make cleaner, more conservative acquisitions.You can negotiate based on condition, not desperation.We’re seeing homes sit 40, 50, even 60+ days in price ranges that used to evaporate in a weekend.

Same goes for cleaners, photographers and the supporting operations cast.

No leaks were found but apparently according to him the wrong wood was used.