@Sean Pincus   Sean wish it was that good out here in Portlandia  24% is rare.. 10 to 15% is customary I just hit a 20%  and I have bouncing off the roof with Joy !! 

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.

@Aaron Coplin the seminar was actually pretty informative for a novice, but they rarely explained anything in-depth because they're hoping you'll buy into the Mastery program where the real meaty stuff is.

In this area it's extremely rare to find a condo without an HOA's, unless the complex is wholly owned by one individual/company.

Unfortunately, there is a huge financial price to pay for our mistake.As much as we like to think the grass is greener on the other side, that's rarely the case.

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".