If you decide to self manage and want help with other functions we can totally help out.We also buy and sell real estate (candor realty), have a repair and maintenance company (CMR Construction) (includes snow plowing, lead abatement and full fledged rehabs) If you need any of those support services please let us know.

I bought from a primary homeowner in Indianapolis metro area who took really good care of this home (I did live in this house and rented it out when I moved back to California) and from a flipper in Indy more recently.As far as primary homeowners, they can range from taking really good care of the house to someone who has a lot of deferred maintenance - I renovated a local property that had a lot of issues.  

Who pays for maintenance is determined by the written contract between parties, not a list on the internet.

@Yixin Huang when it comes to accessing the property and maintenance, you want to DOCUMENT EVERYTHING!

Most new investors do not have the stomach for rehabs or the maintenance of owning an older property.

Repairs and Maintenance are not cheap and shipping carpet/furniture/etc to Hawaii calls for huge price premium so I would be sure keep a reserve for replacements.  

Is there any particular maintenance that is required in a regular basis?

If there is no HOA because it has been family run, it will be dicey, but generally if it is a private road, all those on the road are collectively responsible for maintenance and improvements.

It does need maintenance at least once a year with Leather Food or the like to keep it nice.

We get about 200 - 300 maintenance requests every month; I would have to hire a FT property manager just to "walk" the maintenance concerns.