Best regards, This approach is neutral and objective, focusing strictly on the criteria, and avoids discussing any specifics about the applicant’s personal situation.

It's been great - the property is 100% paid off and the house is worth 300-340k generating approx $2300/mo (that's after utilities/management fees etc.)I'm considering selling the property to buy 3 more within the same price range in the same market. 

However, you will get a range of perspectives because several here don't mind and even brag about losing monthly.

Things like a new roof can range - here in Philadelphia where i do a lot of work, our flat rubber rowhome roofs are fairly inexpensive and standard . . .

Garage parking, full privacy fence, and second living area or bonus room would all be needed to get on the higher end of that range.

Rents for medium term rentals usually range from 1.5 times to 2 times the normal rent for a place.

And what is your price range and are you looking for turn-key properties or something along the lines of a "fixer upper"?

Rates will range from Prime (currently at 7.5%) to Prime + 4% (11.5%).

I wouldn’t subdivide based on your objectives.  1.  

Can you articulate the risks you believe you will  protect against and more importantly how this Wyoming LLC will aid in your objective?