If the handyman can’t get those things done in that amount of time they have no business being a handyman.

You have to be a serious individual that takes care business.

We exclusively travel during non-peak seasons, so we would be looking to rent out completely during busy/peak seasons, and would stay at the place during slow seasonsQuestions for the experts out there:1. which development(s) tends to be the best for ROI/have the best occupancy rates?

Our goal is to have a short term rental business and build it over the next several years.

Looking to get into some smaller apartment buildings in the near future.As far as the difficulties of investing in Japan, I of course agree with everything said, but in my case I'm at near-native fluency and own and manage my own business separate from anything real estate related so even without permanent residency I've never had trouble getting a loan (except of course I can't get some govt backed ones like a primary residence mortgage) for business or investing.I'll try to get in touch with everyone local to よろしくお願いします。

This stands true for any/every investment segment in existence; stocks, ETF's, business ventures.

But I really see this as just business-  I want the best market I can get into. 

We have worked hard to build up our systems to manage our business. 

When you say "we," are you speaking about your business or your personal tax returns, or does your business flow into your personal returns because you file as a sole proprietor?  

Only reason I've been doing it is to get 0% business credit card limit increases.