As for the rest of it, you can find a lot of useful tips on past forum posts along with podcasts and youtube material on the topic (BP and other RE sources).We've self managed STRs for a few years.

Cleveland is a great market if you know how to navigate it and have a good property manager.

I like how the City puts everything permit related on a portal for all related parties and contractors to see -- so there is no "he said, she said" down the road, and you can see where they've approved an inspection, or made comments needed to correct a deficiency.  

*I'm a property manager, not an owner, so I do have a 3rd account for business expenses as required here in Oregon.There are a plethora of software/apps out there for managing properties and funds.

@Tony SchmuckerFrom my experience of working with over 400 investors, your strategy to relocate, house hack, and transition properties to management is a strong, methodical approach.

Common deductible expenses include mortgage interest, property management fees, repairs, and even travel expenses related to property management.

I can however relatively quickly add up to a 500 Sqft garage.

I run Blaze Real Estate a property management company in Amarillo.

I work with a property management company in NJ and we see a lot of success with our clients holding long-term rentals. https://www.tvdhousing.com/Welcome to BP! 

You’ll face hurdles like maintaining a steady deal flow, securing funding, managing renovations efficiently, and optimizing your exit strategies.This guide highlights key strategies for investors looking to transition from single deals to a scalable, volume-based distressed property investment model.1.