Offering my sweat labor and about $20k down, he agreed to sell me the house for $50k, which he originally purchased for $25k, after we fully renovated it.

We simply don't "need" the space we have now, and would be better optimized if we rented it out earlier within our timeline.Personally, I think the death of the contracted tenant is enough of a scenario change to justify a move out of my new primary and into that property, but definitely don't want there to be any questions of fraudulent activity as my wife and I have been very aggressive on purchases over the last few years (4 buy and hold purchases in 2020).So, what do you all think? 

To me, its more important to start than it is to find the optimal area.

The renovation for the side that turned over was mostly cosmetic and was ~$5K labor+materials. 

And all this said, it can be highly market dependent for labor costs.  

I also agree that the holidays were a less optimal time to list.

I certainly think we had the potential to maybe do another (5) but beyond that I am at a loss to understand how people are doing it.Some background is that most of these houses are what I call light rehab (i.e. cosmetics, flooring, maybe a roof) and we do a mixture of self-labor along with finding supplemental workers where we can as professional contractors seem to be impractical somewhat from the economic perspective but more so lead time. 

Would it be more advantageous to wait to invest in order to stockpile cash to purchase multiple properties when prices come down or should I get my feet wet and get started with less than optimal numbers to get experience sooner?

I am seeking an experienced tax advisor to help me optimize my taxes for a rental property (actively selling) + multiple small businesses.Property is in the City of Los Angeles. 

Started a conversation with a framer at the Home Depot for labor if I purchased materials.