Kristin,Start having conversations with agents and investors in those select cities and get a feel for the submarkets within.

Unfortunately, we've been self-employed in a non-real estate industry for a LONG time now and we couldn't document our income in a way that was sufficient for our lender - so we did a cash deal instead.I thought the equity in that property and in the home we own outright (about $256,000 in total equity) would be enough to reset the conversation for our next deal, but our lender says existing equity will always be overshadowed in our situation by documented income (or lack thereof.)  

Here are some recommendations for you:Find and connect with other BP members that are in your area: https://www.biggerpockets.com/search/usersSet up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/alertsRead Beginner’s Guide: http://www.biggerpockets.com/real-estate-investingIf you wish to tag someone in the conversation on the forum, type @ followed by their name and then select the name of that person which should appear below the comments box.

For the finer details, I'd suggest reading a book or two and/or speaking with a good real estate agent, lawyer and CPA that understand investing and can help you with many items on your list.

Here are some recommendations for you:Find and connect with other BP members that are in your area: https://www.biggerpockets.com/search/usersSet up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/alertsRead Beginner’s Guide: http://www.biggerpockets.com/real-estate-investingCheck out BP Podcasts: https://www.biggerpockets.com/podcast If you wish to tag someone in the conversation on the forum, type @ followed by their name and then select the name of that person which should appear below the comments box.

But please, I opened this conversation so I can get different perspectives!

I had a wonderful conversation with Lucas about what I need to do to start out.

To paraphrase this idea - your outsourced accounting partner should by performing the work and proactively providing solutions, as opposed to giving you items to research.

@Laura Hines thank you for that link that was good conversation.  

Here in VT, you only have 14 days to issue an itemized list.Good luck!