@Irene Morgovsky what you are experiencing is that rents do NOT increase linearly with property values.Or look at it another way, the pool of renters that can afford higher & higher rents, shrinks faster than a corresponding pool of buyers.You could look into making it a short-term rental to try to improve rental income, but:1) Is it allowed in that area2) STR rates are coming downYou may have to accept "negative income" or sell.

If I/we had started buying investment properties (even 1 a decade) it would greatly have improved our financial wellbeing.Learn from my regret

The main issues are: 1. gross revenue has been less than half the projections the PM initially provided and what is on AirDNA, and 2. gross revenue has dropped 30% from last year to this year despite me investing over $125K in improvements (new pool, new fire pit, new landscaping, new dog yard). 

Essentially, there must be a paid parking footprint in the area already.The ideal asset would cashflow from day one with the ability to add value via technology, operations improvements, and/or NN lease addition (or renegotiation). 

Even though they planned to refi after five years, the seller financing did not require it, it was a 30 year term.Overall I think I did a decent job of evaluating the property (still some room for improvement there), but not the people.

Realtor says another deal fell through because it didn't fit their needs for an event location.We'd be coming in with 20% and look at about $10k in initial improvements. 

This helps break down the purchase price between the land, the trailers (which may qualify as personal property), and any improvements like utility hookups.

Just to update this post, appfolio has done a ton of improvements. we are using it now, we have close to 700 investors and we have had ZERO issues with it.

Her health improved.

I would advise you to look for a house instead of a condo.Condos have many fees, rules and can have expensive assessments for repairs and improvements that you will be forced to pay.Also Condos are a dime a dozen so the competition is fierce which drives the nightly rental rate way down.