I have also have saved almost $50K so far to take a start in this game and also my personal credit score is above 750.I'd like someone to guide me purchasing my first property and want to kickstart with a small property first.

Negotiating is a skill that needs to be practiced and consistently role played to get right.

The screening process plays a big role in the odds of collection.

If it is a working STR, that really plays no part in the sale of the property.

I would not try and play in the gray on this one - keeo your marketing out of those areas.

A 4-plex would be ideal and you could play around with doing 1 long-term, 1 mid-term, and 1 short-term, plus you, if it works on your area to upgrade your income.

If it's a long-term play, the potential savings on PMI with a conventional loan could be significant.Have you compared rates for both options?

Redeveloping into mixed use live/work/play projects has been the most common proposed solution the past few years in my area. 

I don’t mind having skin in the game either, but I know using private money is key to scaling one day and would like to get some experience with it now, even if it doesn’t fund a majority of the deal. 

Maybe talk to the city and see what the process is.Now of course you don't know how things are going to play out.