You think through the major systems in the house (roof, exterior or tuck pointing, hvac, plumbing, electrical, unit turns, common areas) and if they are all new you should be good for a few years (5-10). 

If you are a considerate buyer that demonstrates an ability to perform, off market deals will come to you through those people with whom you have developed good working relationships.

Business Journal (BizJournals) is the main one I read, but you can find others. bizjournals post about the new developments and changes in the city.

You need to know for sure.Even if you raise the rents, the property is still a negative cash flow, so it doesn't make sense.There are always comps.

Should I charge her a prorated amount of the original rent or the increased month-to-month rent for January?

The good news is that it's never to late to start!

I'm sorry you went through that.

Having good schools played huge part in the properties we purchased.  

I never cared what they are making as the assignment fee, as long as I knew the numbers worked on my end.As for a purchase & rehab lender that will finance up to 100% of the wholesaler's assignment fee - I can introduce you to one that finances that and also 100% of the purchase & rehab up to 65-75% of the ARV.As a lender I sometimes receive off-market properties from wholesalers and other sources and share them to our borrowers if they fit what they are seeking.

I have no debt, a good stable job making about $60k+ gross, and $20k saved up with about $10k in my 401k that I'm thinking about using some if not all of it towards the closing costs of the home I want to buy.