If your tenants are being too “hard” on the property and are causing unusually high amounts of problems that might be a different story altogether and then I’d say you need to screen your applicants better.

We're talking fairly major equipment.

Evaluating your options, considering different scenarios, and staying informed about market conditions will contribute to making sound investment decisions.

There's 2 different options for us, both near 70 acres.

so most people will have to be as leveraged as possible to scale (at the beginning). as in, keep your LTV high and focus on buying 'as much' ($$) RE as possible. this is if you're doing a pretty run of the mill REI strategy like buy and hold. i came across an interesting guideline once: if you could sell today and net 7x+ your annual true net cashflow, you should cash-out/refi, or sell/1031. think of it this way: if your portfolio in a year is worth 1m market value, and you owe 600k, and have a lender that will do a portfolio loan at 80% ltv, you could cashout refi and get 200k to play with (minus closing costs). when you compare the now-lower cashflow from the existing portfolio (higher LTV & maybe different rate), to what you can do with 200k cash, THAT'S where it gets fun. maybe you lose 1k/mo in cashflow on the original portfolio (literally just made up a number, idk), but you can gain 2500/mo in cashflow with that 200k.. then doing the cashout/refi earned you a net increase in your monthly profit of 1500/mo, plus you're getting debt paydown and appreciation on "more" real estate, probably getting bigger tax benefits, etc.

I'm trying to figure out which type of investment appeals most to me and my goals - it seems they all do and have different pros and cons that come with them when I sit down to analyze.Like many, my end goal is to escape my 9-5 and be able to live off of my real estate investments.

They are very  different and it’s an important distinction to understand. 

Are there any specifications on dumpster sizes, work hours, safety equipment, etc.?

Everywhere you look and there they are.Everyone needs to start understanding the difference between a motivated seller and an off-market property.

If you want to own a STR (vs just an Airbnb) and grow a portfolio, you want someone doing the same which is very different than just being an Airbnb.