I want to limit my risk as not knowing where the economy may be going.I'm in a similar boat, also 50 with good paying W-2 looking to build a portfolio to help replace that sooner than later.

I don't think we will ever have enough "doors" to replace an income in this time frame, but we would like to get to 5 doors in the next 5 years which we would sell in 10-15 years to help supplement our retirement income.  

Basically, the bathroom has to be gutted and subfloor replaced.

find peoples pain points and add so much value that they cant replace you

Are you trying to replace your income today?

Roof is approx 15 yo. 4 water heaters been replaced in past 5 years. current brings in $5200 month.

If the replacement property has at least as much value in 1245 components, then section 1245 recapture isn't a problem, you can defer the recapture of the 1245 depreciation. 

This was evidently due to a refrigerator that needed to be replaced to stay in compliance for CHMA.

If it goes down (lightning strike) they can replace it. 

So yes, this is my first time having a contractor leave towards the final stage of a project as other work that I've done are minimal like fence repairs, deck replacements, sink repairs, hvac etc.