Up until now, the tenant has rented for almost 4 years and has always signed an annual lease with me. 

Buyers like to buy at a 2 multiple or 1,000,000 based on 500k profit annually after expenses.Go look on bizbuysell.com Tons of businesses for sale that are not 1,500,000 and some of them throw off great cash flow.A purchaser could possibly get owner finance with the note for some down but do not pay an over inflated price just to get financed.

My annual taxes range in the $3500 area for each of my properties.

my cashflow would be $128.00/mo 2) Offer shorter lease terms rather than annual?

Things to consider are annual co-commissions (essentially franchise fees), annual co-commission caps, desk fees, transaction fees, advertising fees, systems/platform fees, training programs, the schedule required, and then access to principal brokers and or mentors.

I'm an investor in Massachusetts and I'm curious if there's a creative way to set up the landlord/tenant account that holds the tenant's security and last months rent deposits in such a way that the annual accrued interest can be paid to the tenant automatically...As of right now I'm required to manually send a check to each one of my tenants on their year anniversary.

However, I also saw that in some cases my Year 1 or Year 2 "Annualized Total Return" was huge - from 65% to 150% in some cases...

This may include such things as paying the property taxes from the IRA and obtaining annual fair market values for reporting purposes.https://www.irs.gov/retirement-plans/retirement-pl...

You need to account for: Lawn care ($25-ish x 20-ish mows per season)Snow removal ($25-ish per plow x 20-ish plows per season)Water/Sewer: ~$240 per quarterHeating oil: Stated oil consumption in the listing is 730 gals annually - I'd confirm this with the fuel vendor if you can.

.$2,135.00MONTHLY INCOME$1,694.08MONTHLY EXPENSES$440.92MONTHLY CASHFLOW14.08%PRO FORMA CAP$9,853.40NOI$22,125.00TOTAL CASH NEEDED23.91%CASH ON CASH ROI13.59%PURCHASE CAP RATEExpensesIncome50% RuleTotal operating expenses:Mortgage expenses:Vacancy:$170.80Repairs:$213.50CapEx:$106.75Electricity:$50.00Water & Sewer:$162.00Insurance:$120.00Management:$213.50P&I:$380.20Property Taxes:$277.33$72,500PURCHASE PRICEPurchase Closing Costs$2,000.00Estimated Repairs$2,000.00Total Project Cost$76,500.00After Repair Value$70,000.00 Down Payment$18,125.00Loan Amount$54,375.00Loan Points$0.00Amortized Over30 yearsLoan Interest Rate7.500%Monthly P&I$380.20Total Cash Needed$22,125.00 Financial Info2.79%2% RULE $15,625.00TOTAL INITIAL EQUITY2.83GROSS RENT MULTIPLIER 2.16DEBT COVERAGE RATIOAnalysis Over Time3% /yearEXPENSE INCREASE 3% /yearINCOME INCREASE 2% /yearPROPERTY VALUE INCREASEYear 1Year 2Year 5Year 10Year 15Year 20Year 30Total Annual Income$25,620.00$26,388.60$28,835.54$33,428.29$38,752.55$44,924.83$60,375.21Total Annual ExpensesOperating ExpensesMortgage Payment$20,328.97$15,766.60$4,562.37$20,801.97$16,239.60$4,562.37$22,307.82$17,745.45$4,562.37$25,134.21$20,571.84$4,562.37$28,410.77$23,848.40$4,562.37$32,209.20$27,646.83$4,562.37$41,717.40$37,155.03$4,562.37Total Annual Cashflow$5,291.03$5,586.63$6,527.71$8,294.08$10,341.78$12,715.62$18,657.81Cash on Cash ROI23.91%25.25%29.50%37.49%46.74%57.47%84.33%Property Value$71,400.00$72,828.00$77,285.66$85,329.61$94,210.78$104,016.32$126,795.31Equity$17,526.25$19,494.41$25,837.43$38,134.84$53,197.53$71,986.64$126,795.31Loan Balance$53,873.75$53,333.59$51,448.23$47,194.77$41,013.25$32,029.67$0.00Total Profit if Sold *-$1,449.73$6,062.22$30,895.02$80,784.39$143,073.13$220,258.21$432,774.81Annualized Total Return-6.55%12.87%19.10%16.62%14.34%12.71%10.60%