Decide why you are investing, create some goals around that, then plan a strategy to hit those goals and milestones along the way. consider you time, energy and capital you have and each of those lifestyle dimensions.

I am currently in market for best rehab insurance that is resonable and reliable incase of any claims.

I can help you with a reliable contractor.

But how would one find reliable contractors to do the repairs etc?

You get the more reliable LTR revenue that could support the building costs and the STR revenue to boost profits.

They provide you a great, reliable service (where services are not skipped or halfway completed) for a good price that is fair to the both of you. 

- Do they include energy tax benefits within their study?

@Alexandra Reeves, in my experience, tape measure or laser measure is about the only reliable measuring device.  

If you are simply replacing physical time with mental energy worrying about your syndication investments, I would not say the trade off is worth it.

Regular long term rent: $750Airbnb ( only opened 2 months ago) : earning about $2800 on a not peak season. looks like it may hit the 4000 mark in April/May peak season....It is no more than 5 hours of work per week if you do it efficiently and find a reliable cleaning crew.