I don't mind breaking even if I have an investment being paid down by others and a place to visit (even if it's in the off season for example: Utah or Colorado in Summer), but I can't justify investing in a place just to say I have a ski condo...it has to make money.  

"You're going to get wholesalers spending all day long justifying their behavior.  

Fees should be clearly stated, easy to understand, and justifiable.

In my market, we're seeing a major increase in the number of new people moving to town so rentals are in high demand which justifies higher rates.

Fees should be clearly stated in writing, easy to understand, and justifiable.

My question is at what point is cashflow high enough to justify purchase price?

Rents are too low to justify the monthly fees.

Hard to justify paying market prices for work (profit already built in to those) and 50% OR MORE?!

The demand and quality/age of houses in those areas drive prices above what can be justified for rentals, as the rent rate doesn't reflect these increased values.In Cleveland, you have 16K houses though, and million plus homes, painting with a broad brush (Cleveland is a good market to invest, Cleveland's housing stock is old) is the same as USA today saying housing is down.

If it's a hot area, with lots of jobs, I'd keep the rate increase 2-3%, and state it's justified based on your taxes and insurance increasing.