With something as big as the short term rental loophole, you want to make sure documentation is buttoned up and you know the tax consequences at the outset

I would also connect with a CPA to make sure that you can do that with no tax consequence to be certain.

I also find that it's easier to place quality tenants when they're dealing with you and not a property management company - a lot of tenants have had bad property management experiences and avoid listings when they see a company with a bad reputation.

Please don't take our reputations as a stamp of approval that negates all risk. 

You need to set expectations and raise their level of concern that there will be immediate consequences if they get more than a few days behind on their rent. 

Started out as a contractor, became a fix & flipper on the side (slowly accumulating a buy & hold SFR portfolio), and then transitioned into notes from there.When my company was buying 2nd mortgages, I'm not sure my background played as much of a role since we were really just buying the paper but with buying 1st mortgages and REO it really can make a difference with determining construction costs, having reputable "boots on the ground" from my previous life, etc.

Lol developers normally can tie up dirt based on reputation in the area.. and like I said substantial non refundable EM in the 6 figure range..

.- Reputation risk if deals fall apart before closing.Why it might feel less stressful:- No rehab or construction headaches.- No need to manage contractors or permits.- Faster cash, get in and out in a matter of weeks.- Lower capital risk since you're not buying the property.Flipping:Stressors:- Managing contractors, timelines, and budgets, and all the ways those can go sideways.- Holding costs (interest, taxes, insurance, utilities).- Market risk, if the market softens during your rehab, profits can shrink or disappear.- Unexpected repairs or inspection issues that eat into margin.Why it might feel more stressful:- Bigger financial exposure, you’re buying and holding real estate.- Delays can cost you real money.- More moving parts, especially if you're flipping multiple properties at once.Flipping is usually more stressful, but it can be more rewarding financially if everything goes according to plan.

Look into their reputation, check reviews, and confirm that they have a proven track record of successfully helping clients.

Trust but verify everything and always consider the asset itself and the consequences of failure.