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.

Colors, quality of paint, how much prep needed, holes patches etc. 

It seems to me that they all whether paid of free, will all have the same exact amount of houses because all the transactions are all public and so they seem to compete with each other based on the quality of the data of the houses, how up to date it is, and the user experience in configuring the how the layout is.

Contractors, unless you have a working relationship with them, normally do not want you bouncing ideas off them.Understand what their hourly rate is, have a discussion with them that you are okay with paying them an hourly rate if they walk the property with you and provide you a scope of work along with an explanation of what you can/can't get away with in regards to improvements.ask them if you go with them, if they can credit you the amount that you paid.Once you develop a working relationship with a few contractors, you can bounce ideas off them and expect quality responses.I do not invest in New York.Best of luck. 

----------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

I used 401k loan to get money for down payment and repairs.

There is no consideration for risks, areas, quality of the house, renovation, or management.  

Unless you find a buyer with a very specific criteria who is willing to pay above the typical 70% - repairs.

Since the price of a multi unit is double or sometimes 3x the price of a single family home, would it be smart to start off with a SFH and scale up from there or just make the leap into a duplex that I can force some appreciation with minor repairs.

If the age of your equipment is older, or it stops functioning, those repairs can also add up.