Does Hard Money typically cost 30-40% of the purchase price?? 

If so you need to fall into the guidelines (for the investor whos funding it) regarding non arms length transactions.The most common scenarios they typically prohibit are:- Gifts of Equity- Bailouts- Leaseback OptionsAt the end of the day it needs to be a legitimate transaction, with legitimate funds coming into close.

For a new agent to land a listing they typically over promise a seller a high price to win it and then spend money trying to find the magical buyer to purchase it.

I'd be able to put 20% down on each and have money left over for some repairs/updates.It seems like I'd initially take on more stress, less initial return but the long term scalability seems great.  

What I see is typically in the $3k - $6k range for those types of properties.

Repairs and maintenance was $3492.50 for the year. 

That, more than anything will help you answer the question "how much do I need to estimate for repairs"? 

We were not able to recover any yard damages due to other damages they had left that needed repair, which empted out their security deposit.

Land Basis for Condos – Typically determined using county assessor records or HOA allocation.3.

Who would typically take care of these?