I have plans to continue to buy more rental properties, complicating taxes further.I need tax help.

However, there is a 3-year buy-back period, which complicates things in NH. 

We might force something to happen early and he is out for the $5k (maybe less) or, like nearly any litigation, there could be unknown complications that turn this into a $50K case.

I already have a place to live so I don’t need to buy a duplex and live in one rent the other.I’m not sure if I should focus on single or multi-family.To be fair I like multi much more but again it is more complicated for a beginner.

That's why you may see 4plexes that could sell at a higher price than a 5plex, since financing is cheaper, down payment is lower, financing options are more and whole process is a lot less complicated for less than 5 units.I think a good strategy would be to try and purchase properties that are severely under market rent for a lower price and try to negotiate with tenants to leave.

Hi @Chris Ng, Yes, option number one is absolutely simpler, less complicated and less costly. 

Not only does this allow the investor to have to sign one PPM while being able to choose multiple investments throughout the year, it enables significant less overhead or complication on the operator side.

With multiple tenants, I'm told it would just be too complicated to do anything else. 

New York Mansion Tax UPDATEPublished on April 9, 2021Taxes in NYC could be really tricky and complicated, especially for Real Estate.

I just had one in Oregon ( I had title insurance and Chicago missed we were landlocked)  these get complicated so the property I bought had 3 parcels 3 homes and a road to the main highway from said parcels that had been there for 40 plus years.However come to find out they were crossing a old Railroad easement done in the 1880s when logs were railroaded into the ports in Portland to move to the various mills.