You are twenty, if you are working while in school and have potentially low costs of living put as much as you can into investment accounts that will grow exponentially, look up Financial freedom retire early as concepts you can adopt and start early, look for house hacking opportunities (aka find a home you can potentially partner with someone to buy or rent in your area with a decent amount of bedrooms, and then rent bedrooms out to friends) Anyways, learning how to put away a majority of your earning into things like Roths, Self directed IRA's or any other potential growing tool while you get your degree in your respective field/ go into working in that field will open up so many doors for investing in 5 to 10 years.

To get back to your systems with ability to scale, unfortunately that is something I have found you can only do with some knowledge and experience. 

I think it's also good to have data entry and reconciliations handled by separate firms, as it will provide a degree of cross-checking.We use CRI Accounting for our accounting, and they do a fantastic job.

You're passive in this respect, and your ability to take losses is limited.2.

However, the problem I had with cozy had was my ability to scale with it.

Golf.When you flip, the first "expense" you always include/calculate is your profit.When you buy a rental, the first thing you always include/calculate is your cash flow.When you do anything in life that leads to the ability to enjoy that life, the first thing you do is "enjoy that life".What am I saying?

You have the ability to make similar returns that a cash buyer would make but you didn't need as much money to get into the deal. 

As we file taxes jointly, this will provide us with the ability to claim all rental activities/losses as active, with the potential to deduct against my W-2 income.Trying to plan ahead for my next move.

But if the house you are looking at is similar in size to the others in the neighborhood, its a desirable neighborhood, and if you actually have the ability to make 100K profit, then it seems like a very good idea to jump on!  

Deposits were also a joke too with duplicate entries and stuff that just made it easier to do a work around by entering it in as the tenant lost all their deposit and then paid the tenant like I was paying a bill and just note that it was a deposit refund.