- How can I️ maintain the most favorable position for a property loan in the future but continue to utilize equity ?

The 1st position mortgage probably has a better rate and a longer amortization schedule I would guess. 

I’m interested in generating passive income through rental properties but also interested in flipping houses from an investment position (I’m not handy at all) - perhaps down the road. 

Podcasts I have on cycle:BiggerPockets (Real Estate)Best Real Estate Investment Advice Ever w/Joe Fairless (Real Estate)BiggerPockets Money (Personal Finance)ChooseFI (Personal Finance)Mad Fientist (Personal Finance)The Side Hustle Show (Entrepreneurship)Fat-Burning Man (Health) Impact Theory by Tom Bilyeu (Personal Development)

Going from $690 to $1000 may cause them to leave, which could impact you via vacancy expenses if those units aren't capable of demanding $1000.

If I were in your position, I would get pre-approved with your preferred lender and start networking with agents.

I’m just trying to think of what would put me in the most advantageous position for moving forward.

And they were the site that broke the 2016/2017 venture capital funding drought, and raised an impressive $20 million.At the same time, most of the investor feedback on them was not positive with several said they would not use the company again.

Point being that not all improvements make sense from a return point of view or the time its would take to make them cost efficient will have a negative impact on your overall return.

As for my thought @Jordan Hamilton the South Florida market on a whole is probably getting near the seventh inning stretch to reference baseball.I only hold SFR and that is my thought, I hear the multi-family game has been fully priced for some time now.In the end, if one is buying to hold long-term and generate monthly cash flow then as long as the numbers work and it cash flows positive it might now matter as much.Be sure to work those numbers though: vacancies, maintenance, etc.