This has left me with about ~$80K real net worth mostly in weighted index funds and money market funds.

I think debt is good if your goal is to scale and grow your wealth.if you will own your personal residence and as a result just be responsible for real estate taxes, insurance and upkeep, your living costs will potentially be low and you don't need much leverage or a bunch of properties to support your lifestyle.If I were you, I would sell the wedding business since it likely is time comsuming since its an actual business.I would not pay off the two other properties since the rate is low.

Realize that 90% of your friends and family will also want a deal and probably think you are rich for owning a vacation home and do not understand that you most likely have a mortgage and bills and upkeep on said vacation home.  

I have been leaning more Montgomery because of the military base and would like to rent to military with the better up keep and responsibilities they have.

My property operates within an HOA, recently HOA has been getting on our case for re-seeding/up-keeping the front lawn.As with most of CO, grass tends to die over winter, so here is my question: What is the best method to up-keep, re-seed and re-develop the front lawn?

A home is going to require minimum $300/month in upkeep costs no matter what (closer to $500 minimum in my experience, $5k-10k per year is what I have averaged in expenses on my SFR's over the past 15-20 years).

Compare the rental revenue to the costs associated with the property, such as taxes, upkeep, and administration.

If they specialize in REI and are good at what they do, they are worth their weight in gold.

That said, you have to weight the pros and cons of each system.

I have some ideas (visa requirements, acreage, zoning (what it allows for), a section for expenses/upkeep, the amount that everything put together breaks down to depending on the number of people buying into it) but hoping for more specifics on the actual property analysis/numbers side of it since I don’t really have much experience and would need to be able to explain it to someone to help me create the sheet.