You used a HELOC already but no clue how much is drawn.My initial thought is you should at least pay off the HELOC before starting.

I was completely caught off guard by the response from the DOT about consulting with them sooner. 

Even if California will not relent on adjusting emission control standards, and the more than 1,000 supplemental workers at the Stellantis Toledo Jeep plant who are expected to rise to full-time permanent status are laid off, on balance, local incomes are rising.For the vast majority of individuals, a home is the largest single investment of a lifetime.

@Max Murin I think you can learn a ton just off of free education with youtube or learning from someone locally and provide free labor.

Other (besides standard depreciation) off the top of head tax advantages of RE:- cash out refi gives tax deferred access to equity- 1031 for investment properties allow deferring of the gains

It sounds like your year is off to a great start.

First off I'll say hilltop is a very large area.

The str will close before the land sells and then I would like to recast the loan to pay off a portion with the land proceeds.  

Property manager started off using my chosen vendors, but as the years have gone by (I left in 2015) some have dropped out and slowly I have just started using the property manager's vendors our of convenienve.

I have been using Reonomy for the past month and have found it very useful for identifying off market properties.