It will cost $50k. 2 units combined bring in $1295 a month, tenants pay utilities.

BP's search function sucks unfortunately so have fun searching for him.Let me tag a few folks for you above:  @David C., @J.

Combine that with the lure of taking advantage of the opportunity to enjoy the company of family, which happened to live about 20 minutes away, not accounting for traffic of course, from my office (i.e., living free…well, I gave them some money, but nothing near market rents).I spent the next four years saving the extra income in the hopes of one day being able to purchase my first property. 

We have the highest combined tax burden in the country and property taxes are a huge part of that.

This is not untrue, but it is limited in it's statement in the sense that in some cases, a warranty & guaranty may not be needed, so looking to the function of the transfer is important.  

Combined, our incomes are over 100k, so we definitely have an advantage there as we look to invest.The plan is that we will form a partnership (of some legal form) so that we can take advantage of both our incomes to scale our business faster, easier, and with potentially less stress and worry (at least financially).

Your question seems to combine the two and they don't really make sense together. 

You have to have enough cash to pay for your holding or carrying costs.And if you want to sell your house quickly specially during the winter, you should combine marketing the property like crazy with offering the house at a 10% below market price.

Combine that with a lot of tire kickers looking for help estimating rehab costs and contractors are wanting compensation for their "free bids".  

It's simply a function of supply and demand.