The renovation budget can be artificially inflated so you can have a "cash pillow" for maintenance or anything else really.The conventional loan for purchase and rehab is the most commonly used by investorsIf you have a company it is also possible to apply for loans but it is necessary to have at least 6 months of activity.

The lawn work will be an issue too, huge yard and its leaf time. 

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

That synergizes well with snow removal and lawn care seasonally.

Quote from @Andrew Lawn: I am a first time home buyer looking to purchase a home/multi-family property.

Do you frequently require subcontract and vendor engagement (lawn care, snow removal, building maintenance, management company etc.) and if so, do you sign contracts and require that you are listed  as additional insured on their insurance policies? 

Artificial Intelligence (AI) has been changing the world as we know it and the real estate industry is no exception.

Probably only for lawn cutting will I find someone on Thumbtack.2.

This is how its done.As a rental rehabber (for my own portfolio) I just need; a decent handyman who can do simple electtrical fixtures, plumbing fixtures, fix leaks etc, an HVAC if I plan on replacing the system, a roofer if I need a roof (rarely), a painter, and a lawn guy to clean up the lawn.