All in all - owning a place to rent to other people is a business, and business decisions need to be made based on that cold hard facts and not on an emotional basis, unless someone wants to quickly go out of business.

Guess what your insurance company will say?

I've learned a ton about the math behind the decision and what the strategy is and what it isn't and updated my opinion accordingly.

My wife and I own a couple duplexes in Florida, however with insurance costs on the rise, we're looking at Wisconsin, which is where my wife is from originally, and we're looking at small multifamily in Sheyboygan. 

Insurance.

You need to carry a special type of health insurance, not the traditional kind.

The decision depends on your access to capital and the level of risk you're comfortable with.If you need support or financing for your future projects, I'm here to help.Best,Drago.

@Chris Kay beleive you can do DSR loans without a job as they qualify the property, not the borrower.You'd still need 20-25% down though.That's where you have a decision:- Pay down the mortgage, setting yourself up for a future refinance to free up your VA Entitlement.OR- Save up for your next acquisition.Only YOU can make that decision as you have to be comfortable with the increasing debt-load risk and the additional time to manage everything.

It's a balance of cashflow and wealth accumulation.One of the goals is to have tenants pay as much of your cost-of-ownership as possible (loans, taxes, insurance, etc.)In high-cost areas, any Class A or B property you buy will usually negative cashflow for the first 3-5 years, until rents rise enough to cover the negative cashflow + rising taxes & insurance.Investing OOS increases your risks because you may not know the market and you can't check on everything/everyone all the time.If you move forward with your buddies, HIGHLY recommend creating a solid Partnership Agreement!

Florida scares me with insurance issues and constant threat of hurricane damage.