For example gravel versus paved roads.

My question is whether there is any difference in buying a multi-family versus a house with an in-law apartment I would rent out.

I probably did 25% of the repairs, while sub-contracting the rest of the work out myself (versus hiring a GC).  

Short term versus long term profits.Best of luck.

Don't complicate matters, what you are seeking is proof of income not proof of wage rate.

Jason - I am working with Freedom Homes out of Troutman NC, a Berkshire Hathaway holding - going to build a mobile home with a steeper roof pitch versus mod to save 15k in build cost - looks just like mod -seems a good deal so far dw 

I'm a bigger fan of SFH versus multi-family.

We'll look at a 300K worth building versus 500K worth building with zero cash flow.So the question is: Twenty years from now, looking back would you be happy to have paid off a 500K building or a 300K building?

You would definitely have to calculate your returns versus alternative opportunities with such a hefty down payment amount to see if it is a good deal for you. 

For reserves, it really depends to on the above, there's a big difference in buying a 2000 sq. ft SFH that is old, versus a small new-ish 800 sq. ft. home.For software - if you have a good PM and they are managing and you have 2-4 units you don't need software per se, but it definitely helps.