Converting your single-family home into a rental property involves several considerations to protect yourself and ensure smooth operations: Establish an LLC:Liability Protection: Holding the rental property in an LLC can protect your personal assets from potential lawsuits related to the property.Tax Benefits: An LLC can offer tax advantages, such as pass-through taxation, where rental income is taxed at your individual income tax rate.Insurance:Landlord Insurance: Ensures coverage for property damage, liability claims, and loss of rental income.Umbrella Policy: Provides additional liability coverage beyond your landlord insurance, offering extra protection.Deductions:Mortgage Interest and Property Taxes: Continue to deduct these expenses.Depreciation: Depreciate the cost of the property over 27.5 years, excluding the land value.Maintenance and Repairs: Deduct costs related to maintaining the property.Property Management Fees: Deduct fees paid to the property manager.Filing Taxes:Schedule E: Report rental income and expenses on Schedule E of your tax return.Separate Accounts: Maintain separate bank accounts for rental income and expenses to simplify bookkeeping.Lease Agreement:Solid Lease Terms: Ensure your lease agreement is thorough, covering rent amount, due date, late fees, maintenance responsibilities, and eviction terms.Legal Review: Have the lease agreement reviewed by a real estate attorney to ensure compliance with local laws.Tenant Screening:Background Checks: Perform credit, criminal, and eviction history checks on prospective tenants.References: Contact previous landlords and employers for references.Property Management:Regular Inspections: Schedule regular property inspections to ensure it's being maintained properly.Maintenance Fund: Set aside a reserve fund for unexpected repairs and maintenance.Moving Out of State:Communication: Maintain open communication with your property manager.

My biggest pain point has been not knowing all the little things that could have helped me out if I put them in the lease that would have helped me snip some of my problems in the butt and for context I am a roockie with only one rental property Tenants will not move in with out all utilities in their name When tenants move out they will sign a move out form for all damages if any over a reasonable amount Tenant will not hang fie traps out side of home those are just personal examples of some of my issues with my one tenant so what would be really help full is some of the little things that you dont even know that you dont know 

and seeking some wisdom for a rookie.Interested specifically in Kissimmee/Orlando/Davenport as Disney market feels familiar to me and it’s generally a cheaper entry point than beach condos.Looking at Regal Oaks (staying here now on vacation myself and enjoying it, though have read mixed things about occupancy), Windsor Hills, and Champions Gate.Goal is to have a second home that I AirBnb out the majority of the year but also can escape to when NYC is ruthless (like now :) hoping to live in the 150-250K range, bonus if there’s a pool (regal oaks has community pool and individual hot tubs), and solid amenities.Other than reading for my life, how can I number crunch and prepare for this?

I would personally encourage you to use debt if you are looking to wait 3 years to get started though.

I acquired them not for investing, but they ended up as investments due to some life changes.

If you can find a partner with the capital and/or lack of time, you can become that go to person on the team to make sure you are making solid decisions on the buy side, especially if your partners are out of state. 

Next to 0 unless it is coming from a personal contact or a HELOC or something like that. 

We run in-person meetups in Northern New Jersey on the first WED of every month, but in July it's the second WED in Morristown.

I personally won't be doing them here in MD, but some people specialize in acquiring those types of properties and I would strongly suggest you to attend local meet ups and try to speak with someone who had done it successfully and never got burned.

Get a life and do your job!