I feel that some of the condos we own have probably peaked or is near peak and it may be prudent to trade up to SFH or MFH.  

Finding trustworthy trades who do what they say they are going to do at the price they say they will do it.

@Richard SnyderDid you spend (1) 750 or more hours during 2018 in "real property trades or businesses" in which you materially participate AND (2) more than 50% of your personal services preformed during 2018 where in the "real property trades or businesses" in which you materially participate?

When it was time to trade up we decided that we would hold it and rent it for an investment.

A good jack of all trades will be worth his weight in gold as most specialty subs aren't interested in coming all the way out to replace a door knob and/or their hourly rate makes maintenance calls prohibitive.

Even as a lender by trade licensed in CA, we've used the FHA loan to buy multi family homes and we keep that loan until we have 20% equity at what point we refinance into a conventional loan with no PMI.

We nubes are not stupid, we can run pro-formas, we can swing a hammer, we can hire trades and we can funds deals.  

As sch C income is "active" trade or business income and falls into a separate bucket, you would not generally be able to offset sch C income with your Sch E losses.The passive actively loss rules generally do not apply to real estate professionals.

I'm a contractor by trade and I got hooked up with a bank doing Hazard claims work for them. 

I do pay someone to mow my lawn, but that is because the time trade off isn't worth it.