I have a loan broker who can help with 2nd position mortgages and I would only look for properties with high loan balances to avoid that scenario altogether. 

Prioritize constructing long-term wealth, striking a balance between immediate rewards and long-term objectives to generate passive income and lasting wealth.

I'm considering assuming this mortgage, either "subject to" or by transferring the property into a trust, where I would then buy a majority share and cover the remaining balance in cash.The complication arises from the fact that this existing mortgage is a VA loan.

PPP is 6 months of interest on 80% of the original note balance, so for this scenario it's about 5-6k.

If he owes a mortgage on it maybe the rate is low and you can buy the property “Subject to” the current mortgage (take over his low rate mortgage and pay him the balance with seller finance at 6% to save you some $$).

I got my first rental with negative cashflow last year.Property price 241k, loan balance 232k Tenant pays rent 1,800$monthly payment 2,050$Spent 5,000$ on improvements.Property appreciated from 241k to 255$ this year.I am not sure whether I should sell it this year or keep for appreciation purposes?

Location: Chesapeake, VA (large military town) Market Value: $360,000Loan Balance: $245,000Equity/Second position note: $115,000 (30 30-year amortization / 10-year Balloon Payment, 6.5% Interest, $727 monthly payment) - Bringing cash for this would save a ton of money for the buyer.Rate: 2.25%Years Left: 26Current Monthly payment: $1,300 (including taxes/insurance)Current Rent: $2,000Scenario 1: -If you were to purchase with a new VA loan at 7% interest at market value your monthly PITI would be approx.: $2,757-If you were to assume the loan and I carried the second note at the above terms your monthly PITI would be: $2,027Saving: $8,760 per year.Scenario 2:-If you were to bring the same $115,000 as a down payment on a conventional loan you would pay: $1,992-If you were to assume the loan and bring cash for equity position your monthly PITI would be: $1,300Saving: $8,304 (with no need to refi in the future)Since this is a hypothetical situation I'm going to give my number based on nat. average homeownership of 13.2 years.

The balance between less rent and no problems has been a difficult balance to find.

A HELOC is not a conventional loan but rather a loan kept on the lenders balance sheet so they can make limit to the number of properties to whatever their rules say. 

But lets say the property does not appraise in 5 years for more and the initial balance is higher than the refinance loan amount, then he will need to put a downpayment to close on the refinance.