It's difficult enough to keep track of one's own immediate area. 

Standard paperwork you know and love, and one spreadsheet that has each property in a row and the particulars (loan balance, rent, 2nd mortgage(s), etc) in the columns.

I’ve had the most difficult time finding any support near these properties.

In CA I can email title company day of the sherif sale and within two hours I’ll get the clear to close title very or detail title report..... i am finding it very difficult here on the east coast

I got a deal for a no interest for 12 months for CC with a flooring company, the rest I put on a capital one card, the balance was only there a couple months so I did not pay too much in interest. 

Getting both properties to close within that time frame seems difficult so we may just end up selling one, buying a lot and building ourselves.  

The drawback is some properties are difficult and expensive to insure.  

2) Is it more difficult to get a mortgage on an investment property even though i would own it free and clear?

If you get a $440,000.00 value as you project, you need to pay the balance down to $352,000.00 3) I would also ask the lender of the 2nd home you bought to just remove the MI, you will have to have it appraised, but it looks like you would have the 20% equity to allow them to remove the MI. 

Negotiations were very difficult mainly because I had won, or thought I won, the auction 3 times in a row.