I am struggling with the following:How to properly value this property considering the condition it is in...How to value an awkward and somewhat unusable acre...it is shaped like a large splinter.Wanting to maintain friendship with my neighbor and respect her and her property while still trying to get the property at a price that makes it a wise investment...Emotionally, I really want this property because of what I would love to do with it.  

Just to avoid an awkward conversation, I wouldn't tell them anything until I had taken more applications. 

I’m about to start 4th year and feel like it would be an awkward time to start investing knowing that I very well could be on the opposite side of the country for residency.

I have a SFH (30318 area code) with awkward stairs to a partial above ground finished basement with exterior entry.

Cash flow is certainly an issue to consider, but if you can afford it, having a PM buys you a bit of a “buffer” from having to deal with tenants directly, and keeps you at a distance from those difficult or awkward situations of being a “hard-***.” 2011 was indeed challenging, and it sounds like you purchased with narrow margins that would not allow for PM.

But a new wholesaler can gain a lot of credibility to their buyers list if they come to the table with a detailed scope of work, have enough pictures so that a GC can bid the process, and can also help out with that awkward situation where a new wholesaler may lose a deal because they have to "bring in a partner to look at the deal", and then "bring in another partner"  Most new wholesalers never get off the ground because they: A) Don't know how to properly comp a deal.

The room was awkwardly silent until he replied, "How do I know you want it?"

Sloped ceilings, low ceilings, and awkward floor plans can create cramped spaces that are less appealing to potential tenants.

Photo #10 (vanity) is awkward.

My shower caulk was damaged and it looked awkward.