Now I am trying to decide to sell (take the long term cap gains hit) versus a 1031 exchange (never done one) or just relist it. 

But if you use multiple emails as I do for my businesses each Gmail account will have its own google docs space, I found it hard to manage all under one roof.

HI Eric,You can always start off by house hacking meaning you live in one UNIT or ROOM and renting out the other vacant units/rooms to offset your monthly mortgage payment.There are several ways to run and make sure you are maximizing your rental income while keeping your living expense as low as possible.

Time will tell.I've always been wary of businesses that cater to a limited market.

Leveraging an owner occupied loan locally most of the time will take far less cash. 

I agree with wanting the first one to be a "win", I'm just concerned that makes it harder to find something that will cash flow.

My company was only a couple of years old at that time, and I was still working a full-time job (working two full-time jobs, really).These are the shirts of men who have to get dressed for work for the day, going into the office from 9 to 5, so to speak.At that time, I was one of those men putting on a shirt and tie.

Then use the rent you generate over time to upgrade if you think it makes sense. 

Having a few "dead" weeks where no one wants to see houses, so you decide to go down the shore for the weekend.

It took us 3 months to remove an illegal mentally disturbed tenant from an apartment who was sub-letting from one of the tenants.