I purchased this before deciding to get in to real estate.I am trying to decide if I should rent the property out or sale it to buy something with long term investment in mind.

I want to know is it more cost effective or easier to purchase the property alone and put it in a mortgage in our name or purchase the LLC from him that holds the property within it.

I'm just beginning but am considering a bigger commitment in the next five years or so by accessing some or even all retirement funds to buy a building (I'm sure people have thoughts on whether or not that is a good idea!).

A lot of our housing stock here has finished basements or in-law suites, so with something like that you can generate significant rental income for an inexpensive conversion. 

Part or all of the rent is covered by the US gov't (take that as you will).

If that’s the case you can buy in the LLC, in your name, or in a new disregarded LLC.

Could it attract squatters, or is it the right move for responsible property management?

Get an estimate from a GC to get a good idea of what is required.Market Comparables: Check what similar-sized homes with finished basements or additional bedrooms are appraising for in your area.

Just google it or come here. 

I want to know is it more cost effective or easier to purchase the property alone and put it in a mortgage in our name or purchase the LLC from him that holds the property within it.