I have been selling off my Baltimore portfolio and I continue to encounter low ball offers and untrained wholesalers who tie up my property while having no one to buy it.

I specialize in 50+ unit apartments and hotels so when I encounter a single or a small multi family with lots of profit potential, I usually decide to wholesale it. 

This was my largest cash purchase to date so that was a little stressful, we are encountering some challenges in the refi stage as lenders don't know quite how to treat the asset.

The problem you'll encounter with local lenders is that you apparently don't reside in the area of the property.

Occupancy fraud, straw buyers, mortgage brokers making ninja loans for commission, or the terrible banksters on wall street packaging MBS, etc - when there is no clear victim I would argue that these aforementioned "unethical acts" would be undertaken by the majority of BPers (or the average individual - however you'd like to look at it) if presented the correct situation/opportunity.Scott, on your mention of premeditation, it strikes me that a truly intended OO who, within one week of closing, takes a job offer in another state would encounter no problems in renting the property out.

Shortly after, my wife and I encountered some pretty hefty medical bills which I am working to pay off in the next 3-4 months.Here is my dilemma. 

What are some of the biggest hurdles professionally that you've encountered and how did you make it over the hurdles?

Do have a look at as much data as you can, but if the data suggests your expenses are going to total 32% of rent or some such, then the data is missing some expenses that you will encounter at some point.

I've not encountered the use of a variable discount rate (although it's an interesting point that you raise) -- perhaps because an investor looking at an opportunity cost is most likely considering the overall return on an alternative investment.

Most Brokers I've encountered who do Property Management don't even own properties themselves and therefore have the worst lease agreement I've ever seen, leaning heavy towards the tenant and not protection of the landlord or his or her  property.