(Approximately 200,000 over the life of the loan)2) What are the pros and cons for him selling the property to me on a land contract as it pertains to capital gains? 

There are plenty of tips and tricks out there but in the end for STR's it all comes down to creating a valuable experience for your guests....all success flows directly from that but you can certainly increase your bottom line by optimizing processes and reducing costs when possible.  

Following are the similarities and differences between the solo 401k and the self-directed IRA.The Self-Directed IRA and Solo 401k SimilaritiesBoth were created by congress for individuals to save for retirement;Both may be invested in alternative investments such as real estate, precious metals tax liens, promissory notes, private company shares, and stocks and mutual funds, to name a few;Both allow for Roth contributions;Both are subject to prohibited transaction rules;Both are subject to federal taxes at time of distribution;Both allow for checkbook control for placing alternative investments;Both may be invested in annuities;Both are protected from creditors;Both allow for nondeductible contributions; andBoth are prohibited from investing in assets listed under I.R.C. 408(m)The Self-Directed IRA and Solo 401k DifferencesIn order to open a solo 401k, self-employment, whether on a part-time or full-time basis, is required;To open a self-directed IRA, self-employment income is not required;In order to gain IRA checkbook control over the self-directed IRA funds, a limited liability company  (IRA LLC) must be utilized.

How much did he gain by selling it?

@Jessica Geisler, You're in a great position because you have something incredibly valuable to offer him - time and flexibility.He needs time to find his replacement property.   

I know your time is valuable. 

At most you have $40k profit -long term capital gains at approx 20% tax is $8k - most likely worst case tax. 

If it is a purchase, with cash, there should be a P&S contract stipulating a certain price, so he'll have a basis to pay his capital gains tax, and for you to create a basis for the half you bought from him, for tax purposes.

In that unfortunately (but potential) situation, you end up having to bring in another contractor (who will get paid), and then still have an equity obligation to your friend.In my experience, partnering with a contractor who brings nothing to the table other than their contracting skills is a situation where the investor has a whole lot to lose and not a lot to gain.

I don’t need to live at the property, just thought it would be an opportunity to get a valuable property and use the line of credit to fund more deals Your thoughts??