Unless you yourself can do design drawings, you will basically be acting as a plan runner just visiting the city, and being the "middle person" could slow down the process.

This will give you some basic info culled from public records.

Basically getting other peoples opinions on something that I'm looking at.

The best you can do is to evaluate it yourself based on the 3 factors and appraiser should use.1) Income approach - project rents and NOI and use a cap rate you feel appropriate to the market.2) Comparables - look for anything similar sold in that area or surrounding areas.3) Replacement - if you're essentially rebuilding it look at the cost of new construction.

As @Cody L. just mentioned, you could be contributing 44k into a project making you much MUCH more on the back end.However, the "Wholesale" is vital if you establish a pipeline of leads.

Are there reasons why I should not allow my tenant to proceed with this project?

See if anyone else is doing Air BNB and what they're charging, so you are dealing with reality when making your projections.

For project management we use Basecamp.

After I complete this project I plan to purchase next in Columbia, Missouri to diversity to a little larger market not too far from home. 

The architect/contractor can help you budget and maximize your project's potential in your specific market - i.e. they can help answer your question on what type of property is best - new home, modular, small lot, etc.