You must report rental income on Schedule E and can deduct rental expenses like repairs, maintenance, property taxes, mortgage interest (allocated between personal and rental use), and depreciation for the rented portion.

Also, I would love to hear from you privately about how things are going for you.

List price: 445,000.DP: 89,000Closing: 8900Total Invest: 97,900Projected mortgage: 2500Rent: 1700 per unit, 3400 totalTaxes: 42Insur: 263CapEx: 100Repairs: 100Vacancy: 100Total expense: 3105Cash flow: 295, 3.1% - 6.0% CoC return. 

Had a quick question.I purchased the property for $500K about 10 years agoI'm selling the property for $575K with the Fire DamageI received an insurance check of $380K for the fire damage.After Paying off the Mortgage + Escrow + Realtor Fee's, I'll be left with about $150K.My question is will I get taxed on this $150K?

A second mortgage or HELOC might allow you to unlock some funds without losing the 3.25% rate.- I recommend avoiding condos. 

I do not understand your remark as related to the DSCR loan.  2 ADUs are not allowed by f/f conventional financing but is not always enforced.Fortunately if you stay with the current tenant without a refi, by the time you pay principle it is likely the rent will have increased enough to absorb the increase mortgage payment. 

Real estate is so localized that most federal based policy changes don't have massive influence.I can see him (semi-)privatizing Freddie/Fannie.

You also cannot use a second mortgage (from HML/private lender) for a 2-4 unit non owner property. 

Housing prices are high, mortgage rates are high, and competition is fierce so revenue is way downIt’s one thing if you bought a while back like many of us did, so your cost basis is much lower.

If you have strong market knowledge and the ability to find deals, working in acquisitions for a syndicator or a real estate private equity shop could be a good fit.