Friends were buying and selling the same property 10 times raising the value from $500k to $10m on condos or office buildings that were never meant to be occupied.

On bigger properties I have seen syndicators raising money. 

If so, just accept what he says and raise the rents in the next 30-60 days via a rental increase.

It's currently rented at $900 per side with the ability to raise it to the to $1000 mark this year and maybe a little higher after that.

That is what the employee gets paid and if he works for himself, or works for a company then he has to charge you no less than $200 per hour and it can easily take 100 to 200 hours to develop, test and debug a very simple piece of software.What exactly do you expect your software to do and that is probably the most-difficult question to answer because people who don't know how to develop software don't exactly know how to describe what they want.

The rent raises they feared are self-fulfilling, immediately.   

Both of these are extremes in the spectrum.While it may seem logical that we can raise rates due to “inflation”, that same inflation is affecting the average consumer’s spending power, which could have a significant impact on whether (s)he takes a vacation, which will reduce overall demand for anything travel-related, including vacation rentals.

If you've paid down your loan for 10 years and have raised rents with the market, you're likely going to be fine.

Regarding building a team - do whatever you can to get your feet wet, to build more experience, and to raise capital.

I'm flustered as to how to realistically get started here (I'm born and raised NYC).