I have no problem with living frugally and smart in order to make my dreams of owning rental properties come to fruition, however the one thing that has been on my mind lately is whether or not I should step off the breaks a little bit and try to enjoy my 20s (obviously you need money to enjoy yourself i.e. travel, vacations, etc.) or if I should just hit the ground running post graduation and save save save so that I can invest and get started with real estate sooner.

Currently, I work at a high-end golf course as an Assistant Golf Professional and have saved a good amount of money by living frugally with a goal of eventually living off of "passive" income sooner rather than later.

Those with lots of amenities like pools and gyms will have higher HOAs to cover the maintenance associated with them. 

So, the sooner the better! 

I'll try serving the pay or vacate notices sooner (right after the 5 day grace period).

I will try and work with some incentives to hopefully have them move out sooner rather than later.

If you need your money sooner, you can put a mortgage against it at the time of purchase, and do a rate and term refinance as soon as the rehab is done. 

I knew I'd be purchasing properties sooner or later but now that it may be happening I'm not exactly sure how to go about the whole thing. 

1: Should I just sell it out right, take the cash and invest in other project and use those returns to pay off the debts sooner than the 4 years projected by my debtor agency? 

He's getting all of his money 10 years sooner, you're building equity much faster, end up saving $300k+, and will get that much more depreciation.The key is that you really do have to plan on this being a long-term hold.