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I was looking at going the self-managing route due to me having a little more experience and mainly finding a great handy-man and GC in the area to help me if repairs were to come up from the tenant.

Then financing for the horizontal ( toughest in my mind to get)Lastly vertical construction funding.and if this all lines up TIME  most places its 1 year to 5 years to get a project approved and ready for vertical.

Even if I start with one property and work my way up from there, I’m certain I can be good at it.

As a direct short-term rehab style ender we lend to NEWBIES 100% of purchase & 100% of the rehab on 1-4 unit properties (in 18 states) up to 70% of the ARV.

Unfortunately we bought it at an auction and cannot rent it out so we fixed it up and are selling it, but with this slow market thought of taking out a refi in order to move onto my next project.

I just got a renewal and the policy went up 67%, makes it hard to consider continued ownership of the property.

@Gaurav Vedi this is very thorough.Did you also evaluate the increased cost of compliance, admin, and time you will need to invest in executing setting this up and maintaining it? 

Closed at a title company I Have the deed I own the house I am looking to pay off the existing mortgage that is not mine. 

While vacation rentals aren't a huge drop in the home supply bucket, they're not nothing, and any reduction in home supply for primary residences will eventually push prices up.