The other option, however, is that I can live more or less for free for the rest of the year between a few family members and friends and save that bit of extra cash towards the purchase.The extra cash could either help me jump on a deal sooner or it could be a buffer/money for potential renovation when I move in.

Doing this for a few years with honest effort will put alot of extra money in your pocket. 

Bonus points if your property can facilitate the construction of ADUs for extra income.

Sell, pocket $200k in equity, appreciation since they bought it, bank 25% for a new deposit in a year once they repair credit, buy two new second hand cars because they need them, pay off credit card debt, put a little extra to the side for increased rent payments for next 12 months, and reorganize to buy in 12-18 months... now they see the light, a chance to move forward, to not stress, and they're lucky the market increased so much... but if they struggle to keep it, struggle to make payments, then 10 months realize they need to sell, would they have as much equity, maybe, maybe not..  

Our two STR's came with locks that require an extra monthly fee if we want to change them remotely. 

If it was one felony in 1994 , with out all the extras it would be a totally different situation

I also tack on a $50 pet cleaning fee because there will generally be some extra cleaning related to pets when they leave.

To us, it's worth the 8% of rents and the extra costs in repairs, and they still cash flow well even with the extra expense.

Build a contingency budget into your plan by allocating an extra 10-20% for these surprises.To get ahead of potential problems, conduct thorough inspections from top to bottom before buying a property.

For example, I have small two teir rolling cart in the movie room/game room that provide extra space for drinks, glasses and ice, etc.