One of my associate mentioned that both me as a seller and the buyer can claim the interest paid every month, but I am not sure if that makes any sense. 

If I can park the 388k ($415-27k) for one year at CD rate of 4.5% and then est 300k (after paying cap gain/depr recap) at 3.0% (assume CD rates lower) that interest income of about 24 months net of ordinary income tax is about the same as my current mortgage.Trying to play devil's advocate and think why selling this year does not make sense. 

Just run the numbers and make sure things make sense.

:As an accountant it makes sense for you to use the desktop version.

Now knowing my MAO, if they counter, I just look to that MAO, does the deal still make sense? 

Testing the entire BRRRR process to see if it's the right strategy for me long-term.building equity through rehab and build out will be best achieved with a lower priced cash purchase---typically wholesale. or word of mouth. depends on the region though. lots of ways to hunt for good BRRRR candidates, but hunting on the MLS typically wont get you low enough prices to make sense....My brother-in-law, who owns a landscaping company in Lee’s Summit, works with a lot of local builders and has been a huge help...This sounds like a great resource for finding subs that will do the work for you independently. most subs can do other types of work as well.If you’ve worked with trustworthy contractors or subcontractors in the Jackson County/MO area (especially those familiar with investment properties), I’d love your recommendations.

In my experience, 40-year terms have rarely made sense.

You can BRRRR the deals that make sense and sell the rest.

With your background in real estate (STRs and assisted living), commercial MAY make more sense and then if there are any residential deals you can take them as well.

The appraisal was the longest hold up but the junior loan officer we were assigned seems to have zero idea what he is doing and zero sense of urgency...