The challenge seems to be having a loan that is high enough to make it worth while for a bank to lend on, then also having the the POF letter in place for our realtor to make solid offers on MLS properties.

That shouldn´t stop a buy and hold investor.There are 115 forum posts relating to sink holes on BP - might be worthwhile browsing through them if you haven´t already done so. http://www.biggerpockets.com/search/topics?

However, to build experience and to position yourself better, it would be worthwhile to do the analysis on this, build a team (which includes a lender), and perhaps find a partner with experience and capital.

If you are learning it maybe that you are making common wholesaler mistakes and not finding enough value in the deals to make it worthwhile.  

Then start the project, and heck no one wants to lose money but if it ends up costing you a few grand when it's all done I would consider that a worth while investment in education and yourself. 

She wasn't ready to sell and may not sell at all, but we talked for quite a while and I'm fairly certain I made a good impression with her.That's not my normal approach, but when they're that close I think it's worthwhile.

Doing some research, but seems like Simpli Safe or something along that line would be a worthwhile investment.

This is not a marriage, you don't have to court them really, but you need to be efficient and worthwhile for them to take on complex transactions.

He told me to put a price that made it "worthwhile NOT to go through the big renovation project."

What have you done in the past and what terms did you offer to generate interest and provide a worthwhile return for your friends or family if you are doing all necessary work?