But I found deals that were good enough, causing me not having to negotiate the market price..... one step at a time, it’s all a learning process.

But during these 5 years of buying all these properties with her needing to sign for them with me at closing (because my DTI wasn’t good enough with just my income and name on the loans), it’s been a major struggle.

For me the deals are the problem, not the buyers, because I would be a buyer myself of a good enough deal.

You are the first one to say a CPA isn't the best at identifying property - are you saying that they are good enough on the back end to come up with values for cabinets, flooring, appliances, etc? 

If your property covers a lot of it, then that may be good enough to start.

Put a good enough deal in front of an investor, they'll jump on it.Best of luck!

If I can find a good enough deal and get some peace of mind about finding a tenant I think I could work up the courage to take the plunge.

Fair enough, but there's more than one way to skin a cat.We're saying over and over that the HELOC isn't magic, it's just a tool to focus your money on paying off your mortgage, it's the fact that you're paying off your mortgage early that's saving you money, etc. etc. but it's not good enough.

If you are considering retiring here yourself, that may be good enough to purchase. 

It admittedly is a bit nerve-wracking, but the numbers on the project are good enough to support the investment and risk.