Easier to do your taxes as well.....Search here about the need for an LLC when starting out or with just a few properties, usually not necessary or recommended (Except by attorneys-sorry Jason :-)

Also not clear if property tax is included in your mortgage?

I was going to talk to CPAs, maybe attorneys, since I need to set up LLCs, do taxes, and advice in general regarding family/generational financial planning, but CFP may be a better route.

The gains are not realized yet, so you can move the equity without paying taxes on it. 

I'm interested in learning all aspects of RE, including self managing property, and maybe get into STR.This being my first deal, I'm not confident in finding more flips, so I want to defer taxes to preserve my profits. 

When and how do we account for my expenses on my taxes?

Many banks handling tax escrow accounts for mortgages have mistakenly thought there was one tax due twice/year or totally missed one of the taxes.Investors should research the SEV and the Non-Homestead property tax millage rates to project what the property taxes will be after adjustment.

Coming from L.A. to Vermont, the RE laws and prop taxes suck...

I use mint for budgeting and keeping track of my expenses, including those which are tax deductible, and find their system extremely intuitive. 

That would need to be specifically addressed in the assignment though.Now it is common that in most real estate transactions that certain fees/expenses are paid for by the buyer (lending fees, half the escrow fee, appraisals, inspections, survey, and attorney fees for the deed of trust) and certain fees/expenses are paid by the seller (title insurance, half the escrow, prorated taxes, prorated rents, deposits, and attorney fees for the deed).Now it is common that in many wholesale transactions, the contract states that the buyer is elected to pay all closing costs.