Remember having a renter is a business, and you just can't "kick them out" when and if you grow tired of them.My recommendation is to buy what you can afford on your income that is cheaper than rent, or buy a lower-priced home and fix up, even if only a cosmetic fix-up.

If your credit score is high, its actually cheaper (I spoke to a loan officer not too long ago and still true) to get private mortgage insurance instead of the Government insurance. 

Also always get a refi loan estimate, we could have likely refinanced out of the hard money loan with a cheaper long term loan and held on to it as a buy and hold even though budget went way over.

Condos seem much cheaper but do HOA fees offset that difference?

In-house is much more cheaper in the long run and reliable.

If it gets any cheaper I'm buying ammo!

Being your own GC is cheaper but it is a lot of work.

FYI, I have really good news the city's code enforcement team gave me some really great solutions to fix my issues at my property and they were so much cheaper than the original SOW.

Is there a good or bad season to start flipping a house (ie houses are cheaper during this time of year, or they sell more during this time of year etc)?

One very large with a huge selection but rather high prices and another much smaller but cheaper one.