My realtor and I have a mutual friend who needs to sell her house and also the lot next to it. I'm trying to think of all possible options and I thought about subject to's. Do realtors ever help with subject to's and ...

You can achieve the same deductions with bonus depreciation.Yes for trucks if they are full-length bed trucks, otherwise there might be some limitations based on the weight.  

For added context, I'm at the stage where not blowing up my financial life is far more important to me than that trying to achieve maximum gains.

You have to start on them as early as possible to achieve them!  

I am absolutely positive real estate investing is how I want to achieve financial freedom, and ultimately, the life I want. 

May be a good hybrid solution to ease the tax filing fees while still achieving asset protection?

Having five properties and seventeen years of experience behind you will allow you to retire from your job accounting and allow you to achieve financial freedom through real estate: wholesale, flipping, or simple turnkey strategies included.

Buy something at retail and do some improvements, barely achieve the 1% rule, but hope to sell it in a year after I do much more marketing, and in the meantime make a bit of cash flow.

Once you've done that, you can then identify the markets that will let you achieve your goals.

Then start backing out your costs to get there until you arrive at your purchase price you can pay to achieve those returns.