The other two have a mix of ideas.   

I see two separate issues.1.

I'll wrap this post by pinging two other Japan-based American investors for their thoughts (until they actually tell me to stop doing this): @Steven E.

(A couple weeks for 1 property every year or two?

We found two contractors and the bid we received to finish the work were higher than the bid we contracted to complete the entire rehab! 

That would be a helpful addition to your plan as you would further reduce your cost of living.Also don’t forget from that $600 you are planning on getting in cash flow you have taxes, insurance, maintenance, capex, and vacancy to consider.With two homes, you may want to keep that extra $20k as an emergency fund rather than spending it on a third property and then be left with no emergency funds.

I still have it in the back of my mind as a way to turn sweat equity and one down payment into two. 

Since the repairs were two owners ago, I would think the town may be a little more lenient with you.With the new kitchen and bathroom, were they existing and just got renovated or were they added on?

If less than two years, cost seg probably isn't a good route.

Also, the whole point of hiring a PM is to handle tenant, maintenance, and rent collection, so if your partner isn’t actively managing but just supervising the PM, IMO not worth having a two people essentially looking over the same tasks.Contributing financially for one person and the other having no financial stake raises decision making questions, such as when to sell, how profits will be distributed, etc.