If you only plan on owning 2-4 properties, then there's really no harm in self-funding them unless you know a better, safer way to make more than the going interest rate on that money (most investment mortgages right now are about 7%, maybe effectively 5.5-6% after taxes depending on your brackets and tax structure).

Think through each aspect of a potential transaction, and how you will respond to the inevitable hiccups, problems, frustrations, and disappointments that occur in every start up business. 5.

If there are any anomalies that occur which require more expensive repairs then that ratio can and will be higher, especially in your first year or 2 of owning a property as you work to get things stabilized. 

The key element is :"the intent of which is the transfer of title"in law, the intent can be the determining factor, it doesn't have to actually occur or be done in a specific manner.You can speed because you have your foot down too hard on the pedal or you can speed because you are going down hill.

I agree 15 years is not a long time but what is occurring is jurisdictions then pass laws to protect the low cost housing.  

So, essentially the money from the ultimate buyer can NOT be used by the intermediate buyer to close on their purchase since that would be using money from a purchase that can not occur until the prior purchase has been completed.  

BTW the turn that occurred 18 months prior was very similar.  

In this case, am I still able to count the inspection fee as a capital loss, even though this expense occurred before I rented out my first property?

Note ADUs do the opposite seeing that small units in small counts is very expensive development.I see nothing in anything you have stated that addresses what i believe has to occur to accomplish your goal. 

When I sell it I will be back at square one, no harm no foul.And I do mean WHEN I sell it.