Our tenant left 5 days before his lease was up and did NOT participate in a walk out inspection even though I'd sent him a move out check list and told him to set up an inspection 2 days before 4/30/2024.   He left be...

IRC Sec 1402 and the related Treasury regs govern income subject to SE taxes.(3) No such thing as "active" income in the context of IRC Sec 1402 and 469.Again, most Airbnb and VRBO belong on Sch E and are not subject to SE taxes. 

In the evening, we would meet with my real estate agent friend for drinks on a terrace in Casco Viejo or at the Sky Bar downtown.

Actually taking the time to dive into, and learn real estate in a way that is scalable is like drinking from a fire hose, and theirs plenty of water!

The only way I would let a tenant paint is if I could set up a lawn chair, grab a drink and watch them for entertainment.

This is the 2 units + 2 ADUs scenario.I am worried Scenario A might push future financing option into commercial real estate only, which will limit my cashout refi options and the future buyer pool.From a lending perspective, since a "Land Use Restriction" is required to be recorded on the Deed to limit rentals to be longer than 30 days, the property thus will not be considered a true "5 unit commercial property" and my worries in Scenario A will not come to pass, right?

It depends on where you are living, how long you think you will be living here, if 3 years is the minimum but a good chance it’s gonna be longer bite the bullet & buy, if 3 years is the max it’s probably better to just rent, regardless nothing will cash flow, the big benefit is locking in your payment, but the value of that depends on the timeline, as far a where that would really depend on your preference’s in price point, do you want urban or suburban living, how big a space, how nice etc?

Best of luck and let me know if you'd ever want to grab a bite or a small drink sometime in the future I'd be more than happy to connect :)- Joshua Killian

(btw my belongings in my office, like the rest of my footprint in the house, will be very minimal: this small desk, quality office chair, + desktop computer. my thought is i’d put the computer in a closet + leave desk out as a workspace for guests; alternatively i could put all office in closet.)

I thought rental insurance covered the tenants personally belongings in case of fire, theft etc?