Although I've looked (and made lots of offers), I didn't realize that it was a whole different ball game trying to secure a loan for a multi-family vs when I bought a condo as my primary residence.I was hoping for feedback on the terms below and if they seem reasonable?   

Is it standard for HMLs to ask for a one-time deposit of $3500 that includes: 1) evaluators going out to property to determine whether it's a good deal, 2) enrollment fee and 3) "skin in the game"?

How much cash flow will it generate and can the property afford to give up 10%, do you have time to manage it yourself, and probably the biggest in my opinion are you wanting to get into this game long term or is this just a 1 time 1 property deal? 

By day I write software and by night I hang with the family, play soccer and (lately) indulge in RE books.As far as REI experience goes, I own 2 investment condos in St.

Call it the ticket to entry to play in the big boys game.

Not greedy, just some of the stories I’ve heard making like 5-7K a month would be a game changer, as I make only roughly 2K per month!

@Brian Hill Hawaii is more of an appreciation market, so the ROI is more of a long term play

@Raul R.I am not an expert in short-term rental rules in NYC.My understanding is that it can only be deemed legal if the host does it in an apartment that is deemed commercial and below 4 stories.With that - I take it that anyone doing a STR in a building 4 stories or more is illegal.Furthermore - people who are doing a STR in a building 4 stories or less where the building is not deemed commercial - then it is illegal.A lot of people are playing outside those white lines.

This is still relatively close to downtown Denver and over the long-term is probably a good play development from Sloan's Lake continues south and will come here eventually.

As long as adequate thought is put forth, any question is game...Bird's eye view here - I would find out how long he/she has owned some of these properties.