The biggest drawback I am having is calculating cost for repairs & finding a reputable contractor for a fair price - I know nothing about renovations right now.  

This can save you from costly mistakes.

At the cost, and given the benefits of most mortgage insurance offerings, is it worth it to pay (however much extra it is)?

True private money is going to cost 10-12% plus deal equity which often makes the true percentage 20-22% on your money vs alternative lending which will be around 12-14%.Here to chat if you want some help comping a deal and putting one together. 

However, selling within a year may result in minimal mortgage paydown, given the substantial transaction costs.

If that property drops 5 you now have another $15k to come up with on top of the closing costs on that property.

I have about 10-15k to play with which should be enough to cover closing costs and have a small bit in reserve If I can't find a Tennant.

I would caution and encourage you to look into the general cost of living difference from where you currently live and where you are looking to move.  

He has come up through the ranks as a wholesaler, then fix and flip, and now targeting missing middle new construction/development deals.I'm beginning to research GCs/investors that do this type of work, and figured it'd be worth exploring the BP network.If you deal in this area directly, or have a connection I could speak to, that would be much appreciated.At the end of the day I am trying to get round number hard cost estimates on 2-4plex/Townhomes.

However, the high-interest rates are significantly affecting my operational costs.