Sounds like you might be better off to cut your ties to this one sooner than later. 

Could you agree to do 5 houses, staying 2 years in each (which would be better for your capital gains taxes)? 

I prefer not to wait two years to provide tax returns.

Many times they cut back the number of policies they write or become more selective, but lately they're just flat out leaving.

We haven't even put the condo on Airbnb or VRBO yet, and we already have almost every weekend from mid October through early December blocked off for friends and family that want to take their families to SDC.

I could have great income streaming for multiple years and then some economic hit like Covid or the next pandemic and work could go out the door for multiple months.It comes down to a fear of losing a bunch of work and not being able to find more, while I have to be paying off property.Thats why I’m debating if waiting a lot longer and saving up a large savings account is smarter.

I could buy a house for $450,000 with a mortgage of $3,000 plus taxes, insurance, and maintenance.

Hello all,Like most people in Cook County, my property taxes have climbed higher again this year.

The property taxes are current and insurance is current.

The last note was that i learned what a series liability is and was curious if i may be better off doing one of those because i have 2 properties and plan to slowly add more (Maryland does not offer series llc but wyoming does).