We spent 10 years and then sailed away on a sailboat paid for with tax free dollars, 3 waterfront vacation rentals paying for the sailing, and a custom built dock in the back of one for when we were in town. 

$10k/m in "consulting fee"?

capital gains tax, seller commissions , other fees, etc?

At some point 8-10 years did a portfolio loan with good tax returns and ended up using a lot of cash and that loan to buy 2 strs in Myrtle- ocean lakes. we currently have 20 units and Two are str's.theres really no short cut, we built a ton of equity by buying at the right time and fixing up ourselves (I'm a contractor).wr bought the two strs in 2020 and 2022.

I have heard that I should have an LLC for each home but it seems administratively burdensome to have 100 bank accounts and 100 different tax filings, credits cards, checkbooks, etc...

Have the deed holder be an entity (the exact entity and state of filing should be determined by your legal counsel with input from your tax professional). 2.

Just trying to understand tax implications. 

Also note, the military and all government employees on assignment are usually exempt from occupancy taxes if they can present you with an exemption certificate.

Taxes would be around $500/year for the land only.  

For the District of Columbia, is there a template or any advice on what works to challenge property tax assessment increases?