I left QBs because the buildium sales rep convinced me that Buildium would handle all the accounting and the property management.

I handle hundreds of insurance claims, resident compensation, crime, and pricing… so I am very familiar with the system and reasons behind policies. 

After looking at your post, I realized it's probably necessary to have a dedicated real estate attorney handle this issue for me since it's serious and I might make a mistake big enough that probably will cost me too much money to fix.

The key is building systems and finding solid property management to handle things while you move around.

My team at Graystone Investment Group works with investors to handle the whole process—finding solid deals, managing rehabs, and long-term property management.I get why you're looking for options closer to home, and Florida has a lot of potential when you find the right markets.

But need to handle the risk of remote investing, and lackluster appreciation.

The most important thing is to know the details of your local program like the back of your hand, then look for loopholes.Just to give you and the other BP'ers a deeper handle on why some TDR programs work and some don't, I just uploaded an excellent study on the topic to my FilePlace at http://www.biggerpockets.com/files/user/ChrisNewma...

Any advice, tips, or examples of how you’ve handled this would be greatly appreciated!

Prioritize properties with strong rental potential and set aside reserves to handle unexpected costs.Finally, familiarize yourself with tenant laws in your target market, especially in Portland, and consult a real estate-savvy CPA for tax efficiency and legal considerations.

Five units and above is a commercial property, and is handled differently in the market.