He said he would do two more and then we wants to wait six months to a year for the portfolio loans to "season" before doing more. 

I specialize in working with out of State investors, and I'd say the most important step is finding an agent who understands your investment goals and property requirements.If you don't find any properties to buy, the rest of the team is a moot point.Interestingly, I think the seasonal nature of the market in Florida can also work to your advantage.

There are some 4 unit buildings in older parts of Westminster 72nd and Lowell-ish as well.You hit the nail on the head about inventory - there is nothing available in the Denver Metro - I just saw today that year Feb 14 vs Feb 15 there were 25% less listings.

So in the efforts to get out there in the field and starting my first deal I came across an old gentleman who is selling his old trailer home.

Usually let needed repairs season a little so tenants don't think that every time they want something piddly done you are there Johnny on the spot.

Things like mold or foundation issues will generally keep most seasoned investors away.

This is a wonderful resource for both new and seasoned investors. 

I spoke with a neighbor recently and he said that idea could turn out to be a nightmare down the road with these older Charleston homes (mine was built in 1930).

There's nothing worse in an older home, not to have it flow properly.Suggest you consider having it professionally staged. 

Some people suggested NYC may be a difficult place to start out so I've been asking seasoned investors what their thoughts are.