Build a solid foundation before taking a step up - each and every step of the way.There’s a way to scale recklessly and there is a way to scale safely.When OPM is involved safe is way better than reckless.Despite a life long career in RE, I scaled as followsBought a few duplexes for my own accountBought a fourplex for my own accountBought 12 units as a JV with some friendsSyndicated 43 unitsSyndicated 30 unitsBought another 12 units as a JVSyndicated 281 unitsThis was over a 3 or 4 year period.and so forth - now I am GP in close to 1000 units with $125M AUM.Even with all that, my sweet spot is 30 to 50 unit properties - they work best for my partners and I and more importantly our investors. 

However I am struggling to understand and evaluate the risks involved with cash out refinancing 2-5 years down the line.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

In the case of GEG, we let our members know we did not have a track record with them - they were new to us and just being tested - and therefore it was even more important to perform thorough due diligence since we can't be involved in the transaction. 

(most hard money loans require 10-15% down depending on the split between purchase price and rehab). but that is both (1) risky and (2) expensive, as you're paying interest every month on 100% of the borrowed funds. private money is fine, you're just bearing a lot of risk and also involving the relationship in your very first deal. 

Since your parents seem open to your involvement, I would start start small. 

You said: "This seems like an odd strategy - purposefully invest in an asset that loses value, with the hope that it will regain value to save a little on taxes... 

Now, if they don't want to do that for whatever reason and don't have anybody to work with who would do that for you, I'd have to agree with you that they'd better invest at home rather than getting involved in something they don't understand.

The other quesiton i have is if private equity is starting to get involved in this market, companies like Apollo & Carlyle, does that change your feelings about getting involved in the space?

Going this route is more involved and that makes it more costly too.