It seems you think the advice is correct or at least on the right bath, have him throw a few deals your way he says will be good, run the numbers and see if you agree. 

Throwing a win win situation to the table, what if we meet for a beer I share all I have learned and you tell me the secret spots to visit in the island?

I'm obviously not going to pull the trigger and throw away tens of thousands or hundreds of thousands of dollars on something I am not confident in. 

Brought in a boiler service company, they spent 2 days troubleshooting the system and were able to get all but 2 to work, so now 16 out of 18.They have been doing this for 25 years and have no idea what is wrong with the remaining two, and I am considering replacing them with electric baseboard instead of continuing to throw money at this.My bill so far is $2800, and by the time it is all said and done I imagine it will be almost $4000.Do I have any remediation possible?

Throwing this up there.

Or that we throw our guests beers.

I do think your maintenance expense is low, unless you're not including CAPEX, in which case you need a separate category for that.As has been alluded to above this comment, this is not just a market where you can throw dumb money at an object and just wait for the money to roll in.

@Robin GravlinAssuming you don't need income to support yourself, throw all your surplus cash flow at one of your two current loans. 

Throw in realtors fees at 7% for 33.6K and you are writing a check at closing for $43,6000. 

Im not saying I agree at all, I was just throwing it out there as an argument for that side of your dilemma.