You are intentionally trading time for money to make the numbers work.

Hello - I listed one unit (my unit) in south loop a month ago- had a ton of activity in August but both the 2 potential tenants who both paid for background checks fell threw! What luck right?September is crickets.. A...

My opinion for what it's worth, Account Closed, is that it's much harder to find a deal now and make the numbers work.I believe there is more "investors" or at least people attempting to invest than ever before - combine that with our current situation of higher than what "most of us" are used to and low inventory = 10X harder to find good deals - in my opinion.Wholesaling being easy is a myth...I know so many people here in Chicago who talk about it, but the number of people doing it at any scale for a length of time is nearly zero....the one guy I know who's been at it longer than most here in Chicago is @Zach Shepard and he's a silent snipper!

Do more research on the commute time to DC and I95 high traffic sections.

I have heard section 8 can be 2-3 months at times, but sounds like your turnaround time is great. 

I was working as a lead carpentry for a remodeling in company in Seattle, but left in Oct. 2023 to help with my family's property and turn my side work full time, which is slowing down.

So the question is going to be where you think rates will be in 5 years and if it will warrant a refinance at the time. 

There wasn't a firm decision that he made at that point in time, hence things were undecided and unsettled. and not at any point in time, Tenant sent a written letter of move out intent/notice until recently, mid-August '24, when I got the first written "move out notice" from him via "email" that he ll vacate the house on Sept 01 and that the payment will be left on the counter.

I'm also looking for STR insurance and having a hard time finding a company that will insure.

I'd love to get a 2-4 unit for my first purchase.