He rented out the entire house by the room and slept in his camper van in the side yard even in the middle of winter.

A dumb assss property manager that could care less about you or your property, will load it up with grimmy tenants who destroy your property for fun. 

The only draw back I have seen is they are hard to fill during the winter months.

It's fun to flesh out my thoughts and hear others' as well. 

Taking bare dirt and either building Self Storage or setting up subdivision lots for sale is a lot of fun.

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 just recently moved back home to NJ for work and decided to move back in with my parents (not fun but ironically closer to where my job got transferred rather than getting a place) so I am saving a ton more money that will hopefully enable me to make my first deal this year.

I could write a book on it.. and maybe i will one day.. but for fun watch Glenn Garry Glen Ross that is the land business of which i grew up in..

The house on the beach in Edisto was perfection but the sand was rough and the surf and tide was aggressive (too much for the kids to swim half the week but had fun anyway). 

. $500 deposit, monthly rent (I changed it for the winter months and LT) plus signing a proper rental agreement for the 90 days.