Honestly if you want to invest, you are better off having a 9-5 that will give you a good, regular income and allow you to buy rentals. 

When it comes to renting to Section 8 (S8) tenants, there are definitely pros and cons to consider:Pros of S8 Tenants:Guaranteed Rent: The government will pay a portion (sometimes all) of the rent, so you'll have consistent cash flow.High Demand: There's often a waiting list for S8 housing, meaning less vacancy time.Cons:Property Inspections: Your property will need to pass regular inspections, and repairs/maintenance must meet specific standards.Tenant Screening: Just like with non-S8 tenants, tenant quality can vary, so thorough screening is still essential.As for the down payment, yes, most lenders will require 15-25% down for investment properties.

Once you generate these investor leads, your priority should be to follow up with them regularly through call, text, email and in-person meetings. 

As a sideline to a regular local self-managing small landlord in my position, oh, very much so.Anyway, Steve, I'll send you a connection request.

Start-up costs are also deductible but are amortized over 15 years with a limit of 5k.Start-up costs have strict rules and your case might not be the same as this one.Case Summary:Timeline line of eventsStarted investigating property: FebPut first contract (canceled): MayBought first property: December 30thWhether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business:Whether the taxpayer undertook the activity intending to earn a profit;Whether the taxpayer is regularly and actively involved in the activity; andWhether the taxpayer's activity has actually commenced.On the basis investor testimony, we may assume that he undertook this activity to make a profit and that he regularly and actively engaged in it.

A 1031 exchange costs very little as it fits into your regular closing costs.

Then there's other factors to success especially in a heavy lift like this, some of the most important in my opinion are Being on site regularly to manage the contracting processHaving a lot of cash reserves - 'a lot' imo would depend on how thorough your current bids are and how old the property isYou mentioned it's bleeding cash now, whatever your timeline is for the property bleeding I'd double it and see if it still makes sense. 

It seems like it's something people do on the regular, and the lender doesn't usually trigger the due on sale clause. 

What you've shown here is not really a cause for concern in my eyes, however I see much worst conditions regularly.

Property Management Company we work with right now to manage is fine with regular rental but I am having hard time working with them on student rental where some of the regular renting rules don't generally apply.