However, after 2-3 months of researching/self-educating, an opportunity presented itself in that a friend from the gym bought a new house, but it was contingent on them selling their current.

Preliminary research shows costs of coverage that are 3x to 4x that of my current employer.So my question, to those who are self employed or successfully walked away from your W2, how are you handling health and dental coverage?

I'm a huge fan of DSCR loans because they allow real estate investors not to be constrained by a debt to income ratio, which is a challenging calculation for self-employed folks, particularly real estate investors who tend to have a significant portion of their net worth 'off balance sheet' in their real estate.

@Anna NguyenDid you invest with self-directed IRA or self-directed Solo 401k? 

With a single rental I would highly consider self managing until you build your portfolio.

Finally, if you have investors using Self-directed IRA funds, factor in at least 1-2 weeks (another trust custodian told us to count on 3 weeks!)

I'm looking to purchase rental properties but have been self-employed for the past year and have been told by 1 lender than there is a 2 year minimum.

This shows the value of having title insurance, but as I also have posted in the past, unless you get a policy for the value of your purchase price plus the value of the improvements you plan on making, you'll be self insured for the latter if the fraud comes to light after you've started the rehab.Fraudsters target property owners in historic Black neighborhoods in South Florida (local10.com)

Do you flip your self or do you work with an investor? 

Just made an offer on a vacation rental property and plan on using Self Directed IRA to fund it.