One was conventional financing and the other was a portfolio loan from a local bank here in Hawaii, I also did a lot of research into DSCR loans during my search.I'm also an agent here on Oahu but focus mainly on Property Management, at the brokerage we manage roughly 50 units that are a mix of STR, MTR, and LTR's. 

It's best to have a property manager involved because they usually know the rules etc.

They'll have a network of tenants, professional marketing and they know pricing better than a self manager will. 

You have tax benefits through depreciation and you are gaining experience via property management.  

I highly recommend you study this, practice it, and apply it.https://www.biggerpockets.com/blog/rental-property-cash-flow...Property Details:Type: Single-family homePurchase Price: $289,900Down Payment: 20% ($57,980)Loan Amount: $231,920Interest Rate: 6.85%Loan Term: 30 yearsMonthly Mortgage Payment:Using a mortgage calculator, your principal and interest will cost $1,515 per monthRental Income:Average Rent for Single-Family Home: $2,171 per monthOperating Expenses:Property Taxes: $300 per monthInsurance: $100 per monthMaintenance and Repairs: Budgeting 5% of rental income ($109 per month)Vacancy Rate: Assuming 5% vacancy ($109 per month)Property Management Fees: If outsourced, typically 10% of rental income ($217 per month)Total Monthly Expenses:Operating Expenses: $835Mortgage Payment: $1,515Total Expenses: $2,350Net Monthly Cash Flow:Rental Income: $2,171Total Expenses: $2,350Net Cash Flow: -$179 per monthConclusion:In this scenario, the rental income of $2,171 per month does not fully cover the total monthly expenses of $2,350, resulting in a negative cash flow of $179.

I’d recommend starting by connecting with local investor groups and networking with other professionals in the area.Also, seek out teams that are actively investing and managing properties on the ground.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

It provides basically a tenant portal where you can upload copies of the lease, manage electronic payments, even do other things as well like maintenance requests.

Quote from @Hunter Duplantis: So I have spoken with a friend that manages an apartment complex minutes from mine but is a little nicer. 

If they’re open to living elsewhere, keeping the property as a short-term rental seems like the more profitable long-term play.If you’re enjoying the self-management and the demand remains strong, I’d lean toward keeping this property as an STR and exploring ways to add another.