Looking for guidance or to be pointed in the right direction to figure out how hard of a task is it to convert a 2 family legally into a 3-4 family in Yonkers, NY.

And since you have no debt, you really do not need to do this task. 

Purchasing an investment property increases the level of difficulty of your tax return.Purchasing a house-hack is even more difficult.To make it even more difficult - you plan to make improvements so you have to determine which costs are currently expensed and which are capitalized.Not only have you acquired an investment property but you also acquired a personal residence.As a result, direct expenses towards your investment property and indirect expenses are deductible business expenses that can be used to decrease your net income from rental activities.With all that is said - you are trying to operate a business so I would hire professionals to help you with your tasks.

If after 5 minutes into the conversation you get the feeling that "the meter is running" and the person you are talking to wants to get on to other tasks, try another provider to see if they are more engaging.Hope this helps...

That is going to be a tall task in my location as it is very hard to find any single family homes under 100K. 

Moving the home requires re-certification and is quite tasking. 

And I don’t have a contractor that I think is qualified to take this task on in the way I want it performed.

However, it feels like a dounting task to go from no experience to suddenly managing a house with up to ten units 5 hours away from home.

So I gained some property management experience from doing various tasks for them.

My two cents are as follows...we were tasked by Progress Residential to source and acquire homes for their portfolio in Atlanta but initially they did not want us to manage their homes for the reason mentioned...potential conflict of interest...after about 6 months using other managers with poor results, they came to us and asked us to manage given the fact that they were so pleased with the way we professionally approached the acquisition process.